1,1'-Carbonyldiimidazole → HCID 67825376, compound

HRID 1975353Notes

Reaction equation

HRID 1975353 reaction equation
[CH2:1]([S:3][CH2:4][C:5]([NH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)=[O:6])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:32][CH:31]=1>CN(C)C=O>[ClH:29].[CH2:1]([S:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([N:41]2[CH2:40][CH2:39][N:38]([CH2:37][CH2:36][C:33]3[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=3)[CH2:43][CH2:42]2)=[O:14])=[CH:15][CH:16]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazineHCID 53799998HCID 53799998, compound

Product 1

HCID 67825376HCID 67825376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g of 4-ethylmercaptoacetylaminobenzoic acid are introduced into 30 ml of dimethylformamide, and 1.75 g of N,N-carbonyldiimidazole are added. The mixture is stirred for 10 minutes at room temperature. At 80°, 1.75 g of 1-[2-(4-chlorophenyl)ethyl]piperazine are added thereto. The mixture is stirred for a further 45 minutes at 80°. The reaction solution is concentrated by evaporation and the oil is chromatographed. The hydrochloride is recrystallised from ethanol/ether, yielding 1-[4-(ethylmercaptoacetylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 229°-231°.

Workup

  1. additionare added
  2. stirringThe mixture is stirred for a further 45 minutes at 80°
  3. concentrationThe reaction solution is concentrated by evaporation
  4. customthe oil is chromatographed
  5. customThe hydrochloride is recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-88563ce644ea4a66aad56f90d937ca37
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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