Dicyclohexylcarbodiimide → HCID 14324483, compound

HRID 1460820Notes

Reaction equation

HRID 1460820 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][CH2:17][C:18]1[C:19](=[O:41])[N:20]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([OH:37])=O)=[CH:31][C:30]=2[N+:38]([O-:40])=[O:39])[O:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:42]([O:54][CH2:55][CH2:56][CH2:57][NH2:58])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]>C(Cl)(Cl)Cl>[Cl:16][CH2:17][C:18]1[C:19](=[O:41])[N:20]([C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:37])[NH:58][CH2:57][CH2:56][CH2:55][O:54][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[CH:31][C:30]=2[N+:38]([O-:40])=[O:39])[O:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 655963-(Dodecyloxy)propylamineHCID 199825024-Chloromethyl-5-phenyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-one

Product 1

HCID 14324483HCID 14324483, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After adding 90.8 g of dicyclohexylcarbodiimide to a mixture of 150 g (0.400) of 4-chloromethyl-5-phenyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-one prepared in the above step and 600 ml of chloroform, the reaction was performed for 30 minutes at room temperature. Then, 97.4 g of 3-dodecyloxypropylamine was added dropwise to the reaction mixture and thereafter, the reaction was further performed for 5 hours. The reaction product was purified by a short column of silica gel and the product was recrystallized from acetonitrile to provide 78.0 g of the desired product with a yield of 33.4%. The melting point thereof was 110° C. to 111° C.

Workup

  1. waitthe reaction was further performed for 5 hours
  2. customThe reaction product was purified by a short column of silica gel
  3. customthe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-efe4ea06399448f9931f669fbebc8c01
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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