Phosgene → 1-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamide

HRID 1107250

反応式

HRID 1107250 の反応式
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[C:7]([F:19])=[CH:8][C:9]([Cl:18])=[C:10]([NH:12][S:13]([CH2:16][Cl:17])(=[O:15])=[O:14])[CH:11]=1>C1(C)C=CC=CC=1>[Cl:17][CH2:16][S:13]([NH:12][C:10]1[CH:11]=[C:6]([N:5]=[C:1]=[O:2])[C:7]([F:19])=[CH:8][C:9]=1[Cl:18])(=[O:15])=[O:14]

参加物

4

反応物 2

HCID 6371PhosgeneHCID 11000212N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

生成物 1

HCID 110774021-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamide収率 95.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a stirred solution of phosgene (68 mmol) in 35 mL toluene was added the title compound of Step D (4.2 g, 15.4 mmol) in 80 mL toluene at 0° C. and the reaction was stirred at room temperature overnight. The temperature was then raised to 70° C. for 4 h. After cooling to room temperature, the reaction mixture was filtrated and the solvent was removed under reduced pressure. Drying of the white precipitate under reduced pressure yielded the title compound of Step E (4.4 g, 95%) melting at 101.5-102.5° C. 1H NMR (CDCl3) δ 7.5 (d, 1H), 7.3 (d, 1H), 7.0-6.9 (br s, 1H), 4.64.5 (s, 2H).

後処理

  1. temperatureThe temperature was then raised to 70° C. for 4 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtrated
  4. customthe solvent was removed under reduced pressure
  5. customDrying of the white precipitate under reduced pressure

出典と根拠

ORDレコード
ord-876da175843b498091fe36facd3e0ee5
出典データセット
uspto-grants-2000_05
特許番号
US06060432

関連ノート

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