Aluminum(III) Chloride → N-(5-Sulfanyl-1,3-thiazol-2-yl)methanesulfonamide

HRID 127110Notes

Reaction equation

HRID 127110 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][S:6]([NH:9][C:10]1[S:11][C:12]([S:15]CC2C=CC=CC=2)=[CH:13][N:14]=1)(=[O:8])=[O:7]>C1(C)C=CC=CC=1>[CH3:5][S:6]([NH:9][C:10]1[S:11][C:12]([SH:15])=[CH:13][N:14]=1)(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 20288643N-[5-(Benzylsulfanyl)-1,3-thiazol-2-yl]methanesulfonamide

Product 1

HCID 20288660N-(5-Sulfanyl-1,3-thiazol-2-yl)methanesulfonamideYield 30.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of aluminum chloride (510 mg.) and dried toluene (15 ml.) was added 2-methanesulfonamido-5-benzylthiothiazole (560 mg.) over 5 minutes at 110° C. with stirring, and the mixture was further stirred for 1 hour at the same temperature. After the reaction, toluene was removed by decantation. To the residue was added a mixture of water (20 ml.) and methylene chloride (20 ml), and the mixture was stirred for 30 minutes. Thus obtained insoluble material was collected by filtration, washed with water and then dried to give 2-methanesulfonamidothiazole-5-thiol (120 mg.), mp 185° to 192° C. (dec.).

Workup

  1. stirringthe mixture was further stirred for 1 hour at the same temperature
  2. customwas removed by decantation
  3. additionTo the residue was added
  4. additiona mixture of water (20 ml.) and methylene chloride (20 ml)
  5. stirringthe mixture was stirred for 30 minutes
  6. filtrationThus obtained insoluble material was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6db32b5dbe104d3f9a3e8140f39be55a
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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