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

HRID 9093

反応式

HRID 9093 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e323e0dfaa24bf8871d0a446d323fd4
出典データセット
uspto-grants-2006_08
特許番号
US07091223B2

関連ノート

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