4-Toluenesulfonyl chloride → HCID 86602193, compound

HRID 349390Notes

Reaction equation

HRID 349390 reaction equation
[Br:1][CH2:2][C:3]1[S:4](=[C:12]=[O:13])[C:5]([O:9][CH2:10][CH3:11])=[C:6](O)[N:7]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]1[S:4](=[C:12]=[O:13])[C:5]([O:9][CH2:10][CH3:11])=[C:6]([S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])[N:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86602191HCID 86602191, compound

Product 1

HCID 86602193HCID 86602193, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Bromomethyl-5-ethoxy-carbonyl-4-hydroxy-thiazole (8 g, 0.03 mol) was dissolved in 80 ml of chloroform. The solution was then cooled down to 0° C. p-Toluenesulfonyl chloride (5.7 g, 0.03 mol) was added, followed by slow addition of triethylamine (3.64 g, 0.036 mol) at 0° C. The reaction was monitored by TLC and LCMS. After the reaction was done, solvent was evaporated and the crude product was then purified by column chromatography to give 8.5 g of title product (yield 67%; LC: Retention Time=2.05 min; MS: M+1=421).

Workup

  1. additionwas added
  2. customsolvent was evaporated
  3. customthe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-f08f2686ab1543b699603a59a5a40a8f
Source dataset
uspto-grants-2007_02
Patent number
US07179827B2

Reaction notes

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