Benzylamine → HCID 10309157, compound

HRID 583764Notes

Reaction equation

HRID 583764 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[S:18][C:17]([C:19]([OH:21])=O)=[CH:16][C:15]=1[NH:22][C:23](=[O:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([NH:39][C:19]([C:17]1[S:18][C:14]([CH3:13])=[C:15]([NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:16]=1)=[O:21])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 69693616HCID 69693616, compound

Product 1

HCID 10309157HCID 10309157, compoundYield 92.3%

Procedure

The title compound was prepared according to the procedure described for Example 2 using carbonyldiimidazole (0.26 g, 1.7 mmol), 5-methyl-4-phenylacetylamino-thiophene-2-carboxylic acid from Step 1 (0.29 g, 1.1 mmol), and benzyl amine (0.11 g, 1.1 mmol). Acidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration afforded 0.37 g of 5-methyl-4-phenylacetylamino-thiophene-2-carboxylic acid benzylamide. A sample of the crude product was stirred in 2 M aqueous KHCO3 for several hours, filtered off, rinsed with water, dried, and recrystallized from acetonitrile to give product with a mp 167-170° C.

Workup

  1. customThe title compound was prepared
  2. filtrationAcidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration

Sources & evidence

ORD record
ord-f56f6e6d0f3540b681643ef7662bfc23
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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