Triethylamine → HCID 86737511, compound

HRID 1414025Notes

Reaction equation

HRID 1414025 reaction equation
[Cl-].[C:2]1([N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]([N+]2C=CC=CC=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH2:29][O:30][C:31]([NH:33][CH2:34][CH2:35][C:36]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:45]([OH:47])=[O:46])[CH:43]=3)[NH:38][CH:37]=2)=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>O>[C:2]1([N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]([O:46][C:45]([C:42]2[CH:43]=[C:44]3[C:39](=[CH:40][CH:41]=2)[NH:38][CH:37]=[C:36]3[CH2:35][CH2:34][NH:33][C:31](=[O:32])[O:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:47])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12486269HCID 12486269, compoundHCID 14326577HCID 14326577, compound

Product 1

HCID 86737511HCID 86737511, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 1-[(diphenylamino)carbonyl]pyridinium chloride (1.1 g) in water (10 ml) was added rapidly to a stirred solution of 3-[2-[[(phenylmethoxy)carbonyl]amino]ethyl]-1H-indole-5-carboxylic acid (1 g) and triethylamine (0.6 ml) in water (15 ml). After 0.5 hour, an amorphous yellow solid (1.7 g) was filtered off. A sample (0.5 g) was crystallised from a mixture of ethyl acetate and cyclohexane to give the title compound (0.3 g) as a cream crystalline solid m.p. 137°-138.5° C.

Workup

  1. filtrationan amorphous yellow solid (1.7 g) was filtered off
  2. customA sample (0.5 g) was crystallised from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-adbbc39693aa465eaba98fe4785a7d3c
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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