Oxalyl chloride → HCID 14880517, compound

HRID 1588847Notes

Reaction equation

HRID 1588847 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.[NH2:19][CH:20]([CH3:36])[C:21]([N:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>>[C:24]1([N:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:21]([CH:20]([NH:19][C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:12])[CH3:36])=[O:22])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 72899Indole-2-carboxylic acidHCID 14880493HCID 14880493, compound

Product 1

HCID 14880517HCID 14880517, compoundYield 83.6%

Procedure

Working in a manner similar to that described in Example 9, but starting with 2-indolcarboxylic acid (1.3 g), oxalyl dichloride (1 g) and (RS)-2-amino-N,N-diphenylpropionamide (1.2 g), and after recrystallization in acetonitrile, (RS)-N-(1-diphenylcarbamoylethyl)-2-indolcarboxamide (1.6 g), m.p. 242° C., is obtained.

Workup

  1. customafter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-b7221604bd984e2ca364d0d137e287f5
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

Loading…