Methane → 4-Amino-N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 619064ノート

反応式

HRID 619064 の反応式
Br.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[N:14]=[C:15]([NH2:18])[S:16][CH:17]=1.[NH:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)C(C)=O.Cl.C>C(O)C.[OH-].[Na+].N1C=CC=CC=1>[NH2:19][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:18][C:15]2[S:16][CH:17]=[C:13]([C:4]3[CH:5]=[C:6]([C:9]([F:10])([F:12])[F:11])[CH:7]=[CH:8][C:3]=3[F:2])[N:14]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

参加物

8

反応物 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 8481N-Acetylsulfanilyl chlorideHCID 218455954-(2-Fluoro-5-trifluoromethyl-phenyl)-thiazol-2-ylamine hydrobromide

生成物 1

HCID 98448504-Amino-N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-benzenesulfonamide収率 34.5%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1049Pyridine溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A mixture of 0.5 g of 4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-ylamine hydrobromide with 0.38 g of 4-acetaminobenzenesulfonyl chloride was stirred for 2 hours with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and stirred at room temperature for 30 minutes. The separated solid was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.5 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The 4-acetamino-N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-benzenesulfonamide, which separated upon neutralization with concentrated hydrochloric acid, was suspended in 9 ml of 6N hydrochloric acid and boiled for 36 hours. The mixture was cooled, treated with 30 ml of ethanol and neutralized with 2N sodium hydroxide solution. Recrystallization of the product, which thereby separated, from 20 ml of 50% ethanol yielded 0.21 g of 4-amino-N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]benzenesulfonamide as colorless crystals.

後処理

  1. stirringwas stirred at room temperature for 30 minutes
  2. filtrationsubsequently the active charcoal was filtered off
  3. customThe 4-acetamino-N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-benzenesulfonamide, which separated upon neutralization with concentrated hydrochloric acid
  4. waitboiled for 36 hours
  5. temperatureThe mixture was cooled
  6. additiontreated with 30 ml of ethanol and neutralized with 2N sodium hydroxide solution
  7. customRecrystallization of the product, which
  8. customthereby separated, from 20 ml of 50% ethanol

出典と根拠

ORDレコード
ord-2129ff4e1e1c484ba6b233a1f4f93fbf
出典データセット
uspto-grants-1999_09
特許番号
US05958910

反応ノート

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