Dicyclohexylcarbodiimide → HCID 70510136, compound

HRID 1388940Notes

Reaction equation

HRID 1388940 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[N:10]([CH3:16])[C:11]([S:14][CH3:15])=[CH:12][CH:13]=2)=[O:8])=[C:5]([CH3:17])[CH:4]=[C:3]1[CH2:18][C:19]([OH:21])=[O:20].[C:22]([NH:25][CH:26](O)[CH3:27])(=[O:24])[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:22]([NH:25][CH2:26][CH2:27][O:20][C:19](=[O:21])[CH2:18][C:3]1[N:2]([CH3:1])[C:6]([C:7]([C:9]2[N:10]([CH3:16])[C:11]([S:14][CH3:15])=[CH:12][CH:13]=2)=[O:8])=[C:5]([CH3:17])[CH:4]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19967814HCID 19967814, compoundHCID 20469148HCID 20469148, compound

Product 1

HCID 70510136HCID 70510136, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.1 g of 1,4-dimethyl-5-(1-methyl-5-methylthiopyrrol-2-oyl)pyrrole-2-acetic acid, 0.52 g of N-acetyl aminoethanol, 1.05 g DCC and 0.21 g of N,N-dimethylaminopyridine in 75 ml dry CH2Cl2 was stirred at ambient temperature for 16 hours, concentrated and extracted twice with 10 ml portions of CH2Cl2. The crude product is crystallized from ethyl acetate to yield 0.96 g (70% yield) of acetamidoethyl-1,4-dimethyl-5-(1-methyl-5-methylthiopyrrol-2-oyl)pyrrole-2-acetate.

Workup

  1. concentrationconcentrated
  2. extractionextracted twice with 10 ml portions of CH2Cl2
  3. customThe crude product is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-f70282dd556f49f095acfaed54149dd7
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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