Thionyl Chloride → Profluazol

HRID 432957

反応式

HRID 432957 の反応式
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH2:12][Cl:13])(=[O:11])=[O:10])=[CH:6][C:5]([NH:14][C:15]([N:17]2[CH2:21][C@@H:20]([F:22])[CH2:19][C@@H:18]2[C:23](O)=[O:24])=[O:16])=[C:4]([F:26])[CH:3]=1.S(Cl)(Cl)=O>ClCCl.CN(C)C=O>[Cl:13][CH2:12][S:9]([NH:8][C:7]1[CH:6]=[C:5]([N:14]2[C:23](=[O:24])[C@H:18]3[CH2:19][C@H:20]([F:22])[CH2:21][N:17]3[C:15]2=[O:16])[C:4]([F:26])=[CH:3][C:2]=1[Cl:1])(=[O:10])=[O:11]

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 54019167(2R-trans)-1-[[[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]amino]carbonyl]-4-fluoro-2-pvrrolidinecarboxylic acid

生成物 1

HCID 11037075Profluazol収率 84.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

Crude (2R-trans)-1-[[[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]amino]carbonyl]-4-fluoro-2-pyrrolidinecarboxylic acid (173.43 g) was suspended in 550 mL of dichloromethane and 0.65 mL (0.61 g, 8.4 mmol) of N,N-dimethylformamide was added, followed by the dropwise addition of 58 mL (95 g, 0.80 mol) of thionyl chloride at room temperature, and stirring was continued at room temperature. After 2.5 hours, the mixture became homogeneous. After 22 hours, the mixture was poured into 500 mL of ice-water, the layers were separated and the aqueous layer was extracted with dichloromethane (twice with 75 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (twice with 400 mL), dried over magnesium sulfate and evaporated under reduced pressure to afford 140.69 g of the crude title compound (84.7% yield from the isocyanate).

後処理

  1. customwas continued at room temperature
  2. waitAfter 22 hours
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (twice with 75 mL)
  5. washwashed with saturated aqueous sodium bicarbonate (twice with 400 mL),
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-8b6d9dda3312403785e5f2b8810c6e46
出典データセット
uspto-grants-2003_12
特許番号
US06664400B2

関連ノート

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