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Water → Ethyl 2-(dichloromethyl)-4,5-dihydro-1,3-thiazole-4-carboxylate

HRID 902771
ノート
印刷プレビュー

反応式

HRID 902771 の反応式
[Cl:1][CH:2]([Cl:5])[C:3]#[N:4].C[O-].[Na+].Cl.[CH2:10]([O:12][C:13](=[O:18])[C@H:14]([CH2:16][SH:17])N)[CH3:11].O>CO.C(Cl)Cl>[Cl:1][CH:2]([Cl:5])[C:3]1[S:17][CH2:16][CH:14]([C:13]([O:12][CH2:10][CH3:11])=[O:18])[N:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 18177DichloroacetonitrileHCID 2723617Ethyl cysteinate hydrochlorideHCID 10942334Sodium Methoxide

生成物 1

HCID 67420856Ethyl 2-(dichloromethyl)-4,5-dihydro-1,3-thiazole-4-carboxylate収率 93%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
2 回
HCID 6344Dichloromethane溶媒

実験手順

Dichloroacetonitrile (33.67 mL, 420 mmol) was added slowly, whilst maintaining the temperature below 0° C., over 30 min. to a solution of sodium methoxide ((25% w/w) 9.63 mL, 43 mmol) in methanol (84.5 mL) which was precooled to −10° C. This was allowd to stir for 30 min. before the addition of L-cysteine ethyl ester hydrochloride (78.32 g, 422 mmol) dissolved in methanol (67.4 mL) and then stirred overnight at RT. Water (136 mL) followed by DCM (136 mL) was added to the mixture and stirred vigorously. The organic layer was separated and the aqueous layer was reextracted with a further 136 mL of DCM. This was concentrated in vacuo to give the crude product (94.1 g, 93%).

後処理

  1. temperaturewhilst maintaining the temperature below 0° C.
  2. additionwas added to the mixture
  3. stirringstirred vigorously
  4. customThe organic layer was separated
  5. concentrationThis was concentrated in vacuo

出典と根拠

ORDレコード
ord-decbb317192d4b52a198f9191afcd123
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07365225B2

反応ノート

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