4-Iodobenzenesulfonyl chloride → HCID 22031478, compound

HRID 1792473Notes

Reaction equation

HRID 1792473 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH3:18])[N:17]=1.[CH3:19][Si](C=[N+]=[N-])(C)C>N1C=CC=CC=1.CO.O1CCCC1>[CH3:19][N:12]([C:13]1[S:14][CH:15]=[C:16]([CH3:18])[N:17]=1)[S:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 73994-Iodobenzenesulfonyl chlorideHCID 741432-Amino-4-methylthiazoleHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 22031478HCID 22031478, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

760 mg of N1-(4-methyl-1,3-thiazol-2-yl)-4-iodo-1-benzene sulfonamide obtained by reacting 4-iodobenzenesulfonyl chloride with 2-amino-4-methylthiazole in pyridine was dissolved in a solvent mixture of 5 mL methanol and 3 mL tetrahydrofuran, then 1.1 mL (trimethylsilyl)diazomethane (2 M hexane solution) was added thereto, and the mixture was stirred for 1 hour. The solvent was evaporated and purified with an NH silica gel column, to give 335 mg of the title compound as a pale yellow solid.

Workup

  1. customThe solvent was evaporated
  2. custompurified with an NH silica gel column

Sources & evidence

ORD record
ord-52e3b9d8c58f45aca3d21a2fe05817b7
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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