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Hydrochloric Acid → N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

HRID 432949
ノート
印刷プレビュー

反応式

HRID 432949 の反応式
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.N1C=CC=CC=1.[Cl:20][CH2:21][S:22](Cl)(=[O:24])=[O:23].Cl>O.C(OCC)(=O)C>[Cl:13][C:3]1[C:2]([NH:1][S:22]([CH2:21][Cl:20])(=[O:24])=[O:23])=[CH:7][C:6]([NH:8][C:9](=[O:11])[CH3:10])=[C:5]([F:12])[CH:4]=1
参加物反応条件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 313Hydrochloric AcidHCID 1049PyridineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamide

生成物 1

HCID 10870764N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

1000 g of crude N-(5-amino4-chloro-2-fluorophenyl)acetamide (4.93 mol) which still contained 1 L of ethyl acetate was dissolved in 3900 g (49.3 mol) of pyridine at 20° C. To the yellow solution was added 845 g (5.42 mol) of chloromethanesulfonyl chloride at 20-30° C. over 1-2 hours. The solution was allowed to stir for 1 additional hour. 2300 g of pyridine were distilled off under reduced pressure at 40° C. To the remaining reaction mixture were added 5.3 L of water and 1.7 L of concentrated HCl (pH 3) whereupon the product precipitated. The slurry was cooled to 20° C. and filtered off. The filter cake was washed twice with 1300 mL of water. The product was dried in vacuo at 70° C. to yield 1500 g (92% purity) of the title compound as a solid melting at 210° C.

後処理

  1. distillation2300 g of pyridine were distilled off under reduced pressure at 40° C
  2. customTo the remaining reaction mixture
  3. customprecipitated
  4. filtrationfiltered off
  5. washThe filter cake was washed twice with 1300 mL of water
  6. customThe product was dried in vacuo at 70° C.

出典と根拠

ORDレコード
ord-1b9db3bfb50640d98ef2300492be3d1a
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06664400B2

反応ノート

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