p-Bromobenzenesulfonyl chloride → HCID 69206070, compound

HRID 901960Notes

Reaction equation

HRID 901960 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH2:14][C:15]2[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=2)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 45117596Ethyl 2-(methylaminomethyl)thiazole-4-carboxylate

Product 1

HCID 69206070HCID 69206070, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromobenzenesulfonyl chloride (2.1 g, 8.2 mmol) was added to a solution of ethyl 2-(methylaminomethyl)thiazole-4-carboxylate (1.5 g, 7.5 mmol) and triethylamine (2.1 ml, 1.5 g, 15 mmol) in dichloromethane (30 ml) and the mixture was stirred for 18 h. The mixture was diluted with ethyl acetate and washed with 1N potassium hydrogen sulphate, water and brine, dried and reduced. Chromatography (35% EtOAc/65% hexanes) afforded ethyl 2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carboxylate (2.1 g, 67%) as a white solid.

Workup

  1. washwashed with 1N potassium hydrogen sulphate, water and brine
  2. customdried

Sources & evidence

ORD record
ord-757e8e0983414520884302abbbbb2205
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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