Methanol → 5-Chlorovaleroylamino-2-benzylmercapto-1,3,4-thiadiazole

HRID 1085655Notes

Reaction equation

HRID 1085655 reaction equation
CCN(CC)CC.[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[NH2:16][C:17]1[S:21][C:20]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:19][N:18]=1.CO>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:16][C:17]1[S:21][C:20]([S:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:19][N:18]=1)=[O:14]

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 740895-Chlorovaleryl chlorideHCID 992851,3,4-Thiadiazol-2-amine, 5-((phenylmethyl)thio)-

Product 1

HCID 156659505-Chlorovaleroylamino-2-benzylmercapto-1,3,4-thiadiazoleYield 90%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 ml (13 mmole) of Et3N, 1.38 g of 5-chlorovaleroyl chloride and 80 ml of 4-DMAP are successively added to 2 g of 5-amino-2-benzylmercapto-1,3,4-thiadiazole (8.9 mmole) suspended in 5 ml of anhydrous methylene chloride at room temperature with stirring and under nitrogen atmosphere. The reaction is checked by TLC (10% methanol in chloroform) and it is complete after 3 hours. The solid product so formed is filtered, washed with water and purified by crystallization from ethanol. 2.7 g of 5-chlorovaleroylamino-2-benzylmercapto-1,3,4-thiadiazole is obtained with melting point 145°-148° C. and 90% yield.

Workup

  1. customThe solid product so formed
  2. filtrationis filtered
  3. washwashed with water
  4. custompurified by crystallization from ethanol

Sources & evidence

ORD record
ord-b76f5b753f924e5f957d9c8d832f8932
Source dataset
uspto-grants-1991_04
Patent number
US05010204

Reaction notes

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