Methanesulfonyl chloride → HCID 15729162, compound

HRID 1656963Notes

Reaction equation

HRID 1656963 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:13][CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15729149HCID 15729149, compound

Product 1

HCID 15729162HCID 15729162, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-acetamido-5-(4-aminophenylthio)thiazole (3.2 g) in pyridine (64 ml) was added methanesulfonyl chloride (1.52 g) at 5° C. with stirring. The reaction mixture was stirred for 3 hours at 5° C. and concentrated in vacuo to give solid. The solid was subject to column chromatography on silica gel (silica gel, 70-230 mesh; Merck: 200 g) and eluted with a mixture of chloroform and methanol (50:1) and eluted with a mixture of chloroform and methanol (20:1). The fractions containing the objective compound were combined and evaporated to dryness in vacuo to give 2-acetamido-5-(4-methanesulfonylaminophenylthio)thiazole (4.0 g, yield: 96.6%). mp: 236°-239° C.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at 5° C.
  2. concentrationconcentrated in vacuo
  3. customto give solid
  4. washeluted with a mixture of chloroform and methanol (50:1)
  5. washeluted with a mixture of chloroform and methanol (20:1)
  6. additionThe fractions containing the objective compound
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d6ff0ffdfe644ecd9558d1e43f67e1dc
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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