1,2-Dichloro-3-isocyanatobenzene → 5-Tert-butyl-2-(3-(2,3-dichlorophenyl)ureido)thiophene-3-carboxylic acid

HRID 18919ノート

反応式

HRID 18919 の反応式
[C:1]([C:5]1[S:9][C:8]([NH2:10])=[C:7]([C:11]([OH:13])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[N:22]=[C:23]=[O:24]>C1COCC1>[C:1]([C:5]1[S:9][C:8]([NH:10][C:23]([NH:22][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=2[Cl:14])=[O:24])=[C:7]([C:11]([OH:13])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 534291502-Amino-5-tert-butylthiophene-3-carboxylic acid

生成物 1

HCID 586793735-Tert-butyl-2-(3-(2,3-dichlorophenyl)ureido)thiophene-3-carboxylic acid収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a vial containing 5-tert-butyl-2-aminothiophene-3-carboxylic acid (1 mmol) in THF (7 mL) was added 2,3-dichlorophenyl isocyanate (1 mmol). The vial was capped and the solution was stirred at 70° C. for 21 hours. The reaction was cooled down to room temperature and the solvent was removed under vacuum. The oil residue was treated with dichloromethane and the resulting mixture was left to stand at room temperature for 1 hour. The solids were filtered, washed with minimal amount of dichloromethane and dried under vacuum to yield the expected 5-tert-butyl-2-(3-(2,3-dichlorophenyl)ureido)thiophene-3-carboxylic acid (317.2 mg, 83%). Coupling with the appropriate amine was performed as described above for Example 1.

後処理

  1. customThe vial was capped
  2. temperatureThe reaction was cooled down to room temperature
  3. customthe solvent was removed under vacuum
  4. additionThe oil residue was treated with dichloromethane
  5. waitthe resulting mixture was left
  6. waitto stand at room temperature for 1 hour
  7. filtrationThe solids were filtered
  8. washwashed with minimal amount of dichloromethane
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-8027bc2a9abd4f80b73ba54cf7c729c5
出典データセット
uspto-grants-2010_06
特許番号
US07741479B2

反応ノート

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