Water → 5-Thiazolemethanol, 2-bromo-4-methyl-, 5-methanesulfonate

HRID 2233311Notes

Reaction equation

HRID 2233311 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH2:8][OH:9])=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>ClCCl>[Br:1][C:2]1[S:3][C:4]([CH2:8][O:9][S:18]([CH3:17])(=[O:20])=[O:19])=[C:5]([CH3:7])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59295463(2-Bromo-4-methylthiazol-5-yl)methanol

Product 1

HCID 592955205-Thiazolemethanol, 2-bromo-4-methyl-, 5-methanesulfonateYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of (2-Bromo-4-methyl-thiazol-5-yl)-methanol (3.2 g, 15.6 mmol) and triethylamine (3.2 mL, 23.4 mmol) in dichloromethane (80 mL) is slowly added a solution of methanesulfonyl chloride (2.1 g, 18.7 mmol) in dichloromethane (20 mL). The mixture is kept at this temperature for 45 minutes and afterwards allowed to warm to room temperature. Water (30 mL) is added after 3 hours and the mixture is extracted with ethylacetate. The organic phase is separated and dried over MgSO4. The organic solvent is removed under reduced pressure to give 3.0 g of Methanesulfonic acid 2-bromo-4-methyl-thiazol-5-ylmethyl ester, which was used without further purification.

Workup

  1. extractionthe mixture is extracted with ethylacetate
  2. customThe organic phase is separated
  3. dry with materialdried over MgSO4
  4. customThe organic solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b3b963e91f604cc78be468651749bdd1
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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