Phosphorus oxychloride → methyl 2-chloro-1H-1,3-benzodiazole-7-carboxylate

HRID 1505793ノート

反応式

HRID 1505793 の反応式
O=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[NH:3]1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[N:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 22745204Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate

生成物 1

HCID 68407476methyl 2-chloro-1H-1,3-benzodiazole-7-carboxylate

反応条件

温度
120 °C

実験手順

A solution of methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (prepared as described in US2009/186879) (2.0 g) in phosphoryl chloride (18 mL) was stirred at 120° C. for 2.5 hours. Excessive phosphoryl chloride was removed under reduced pressure. To the residue was added saturated aqueous sodium bicarbonate under ice-cooling, and it was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified on column chromatography to obtain the titled compound (1.5 g) as white powder.

後処理

  1. customExcessive phosphoryl chloride was removed under reduced pressure
  2. additionTo the residue was added saturated aqueous sodium bicarbonate under ice-
  3. temperaturecooling
  4. extractionit was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified on column chromatography

出典と根拠

ORDレコード
ord-59bb7b8c8ada4687a64bb879afddaffd
出典データセット
uspto-grants-2015_12
特許番号
US09216968B2

反応ノート

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