| C1408 | 2-Chloro-1,3-dimethylimidazolinium Chloride (DMC) (1a) |
25g 5g |
| C1639 | 2-Chloro-1,3-dimethylimidazolinium Chloride (ca. 25% in CH2Cl2) (1b) |
25g |
| C1651 | 2-Chloro-1,3-dimethylimidazolinium Hexafluorophosphate (CIP) (2) |
5g |
DMC (1) has been reported by T. Isobe and T. Ishikawa as a powerful dehydrating equivalent to DCC. The dehydrating reagent 1 is applied to the esterification of hindered alcohols1), conversion of aromatic oximes and carboxamides into nitriles1) and construction of heterocycles2) under nearly neutral conditions. Moreover, it is applicable to chlorination, oxidation, reduction and rearrangement under nearly neutral conditions3). The resulting cyclic urea 3 byproduct can be removed easily by washing with water.
The reagent 1 gradually decomposes with moisture in the air so that extra care in handling is needed. However, DMC in dichloromethane 1b is easy handled using a syringe. In addition, CIP (2) can be used like 1 and it is more stable than 1 against moisture.
References
T. Isobe, T. Ishikawa, J. Org. Chem., 64, 6984 (1999).
2) The construction of heterocycles through dehydration reactions
T. Isobe, T. Ishikawa, J. Org. Chem., 64, 6989 (1999).
3) Utility for chlorination, oxidation, reduction, and rearrangement reactions
T. Isobe, T. Ishikawa, J. Org. Chem., 64, 5832 (1999).
4) Stability of CIP
K. Akaji, N. Kuriyama, T. Kimura, Y. Fujiwara, Y. Kiso, Pept. Chem., 29, 193 (1992).
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