1,1'-Carbonyldiimidazole → Hydrochloric Acid

HRID 1975355Notes

Reaction equation

HRID 1975355 reaction equation
[CH2:1]([S:3][CH2:4][C:5]([OH:7])=O)[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:20][NH:21][C:22]1[CH:44]=[CH:43][C:25]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)[CH2:30][CH2:29]2)=[O:27])=[CH:24][CH:23]=1>CN(C)C=O>[ClH:42].[ClH:42].[CH3:20][N:21]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([N:28]2[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][C:36]3[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=3)[CH2:32][CH2:33]2)=[O:27])=[CH:43][CH:44]=1)[C:5](=[O:7])[CH2:4][S:3][CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69387Ethylthioacetic acidHCID 19020574HCID 19020574, compound

Product 2

HCID 313Hydrochloric AcidHCID 67825098HCID 67825098, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.3 g of ethylmercaptoacetic acid are dissolved in 25 ml of N,N-dimethylformamide, and 2.3 g of N,N-carbonyldiimidazole are added. After 15 minutes at RT, the mixture is heated for 5 minutes at 90° ET. Then 3.5 g of 1-[4-(N-methylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine (see European Patent Application No. 489 690, Example 9) are added thereto, and the reaction mixture is kept at 110° ET for 14 hours. The mixture is concentrated by evaporation and the oil is chromatographed over silica gel (eluant: dichloromethane/acetone 8:2). Treatment with alcoholic hydrochloric acid yields 1-{4-[N-methyl-N-ethylmercaptoacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 163°-164°.

Workup

  1. temperaturethe mixture is heated for 5 minutes at 90° ET.
  2. customis kept at 110°
  3. customfor 14 hours
  4. concentrationThe mixture is concentrated by evaporation
  5. customthe oil is chromatographed over silica gel (eluant: dichloromethane/acetone 8:2)

Sources & evidence

ORD record
ord-eb26b763a35240d1b8aa745e55b54cac
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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