Ethyl chloroformate → HCID 86695275、化合物

HRID 709412ノート

反応式

HRID 709412 の反応式
ClC(OCC)=O.[CH2:7]([O:9][C:10]([C:12]1[S:13][C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=1)=[O:11])[CH3:8].[N-:20]=[N+:21]=[N-:22].[Na+]>CC(C)=O.O>[N:20]([C:17]([C:14]1[S:13][C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])=[N:16][CH:15]=1)=[O:19])=[N+:21]=[N-:22]

参加物

6

反応物 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 667149792-(Ethoxycarbonyl)-1,3-thiazole-5-carboxylic acid2 回

生成物 1

HCID 86695275HCID 86695275、化合物収率 75.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

Ethyl chloroformate (9.8 g, 83.6 mmol) was added to a solution of 2-(ethoxycarbonyl)thiazole-5-carboxylic acid (Intermediate X, 13 g, 64.67 mmol), TEA (9.79 g, 97.01 mmol) in acetone (130 mL) at −20° C., stirred for 1 h, then a solution of NaN3 (5.4 g, 83.6 mmol) in water (15 mL) was added and stirred at RT for 30 mins. After completion, the solvent was evaporated, the crude residue was diluted with water (150 mL) and extracted with EtOAc (2×150 mL). The combined extracts were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford Ethyl 5-(azidocarbonyl)thiazole-2-carboxylate (11 g crude) as brown liquid. The crude was carried to next step without further purification.

後処理

  1. stirringstirred at RT for 30 mins
  2. customAfter completion, the solvent was evaporated
  3. additionthe crude residue was diluted with water (150 mL)
  4. extractionextracted with EtOAc (2×150 mL)
  5. washThe combined extracts were washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-a5a4cd7d3c9d4c828b014b773f3378a2
出典データセット
uspto-grants-2015_11
特許番号
US09181198B2

反応ノート

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