Methanesulfonyl chloride → Ethyl 4-methyl-2-[(methylsulfonyl)amino]-1,3-thiazole-5-carboxylate

HRID 9093

Reaction equation

HRID 9093 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>ClCCl.N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][S:14]([CH3:13])(=[O:16])=[O:15])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 2989996Ethyl 4-methyl-2-[(methylsulfonyl)amino]-1,3-thiazole-5-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (558 mg, 3 mmol) in dichloromethane (15 mL) and pyridine (5 mL) was treated with methanesulfonyl chloride (687 mg, 6 mmol) at rt overnight. The solution was diluted with dichloromethane (50 mL) and washed with 2N aq. HCl solution (15 mL, 3×), dried (MgSO4), filtered and concentrated. The crude residue was diluted with ether (25 mL) and the solid was filtered, washed with 1:1 ether:hexane mixture (10 mL, 3×), and dried in vacuo to obtain the title compound (687 mg, 87%) as an off-white solid.

Workup

  1. washwashed with 2N aq. HCl solution (15 mL, 3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude residue was diluted with ether (25 mL)
  6. filtrationthe solid was filtered
  7. washwashed with 1:1 ether
  8. dry with materialhexane mixture (10 mL, 3×), and dried in vacuo

Sources & evidence

ORD record
ord-8e323e0dfaa24bf8871d0a446d323fd4
Source dataset
uspto-grants-2006_08
Patent number
US07091223B2

Linked notes

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