Hydrochloric Acid → 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 217074ノート

反応式

HRID 217074 の反応式
CO[C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:8]2[N:9]=CNC=2[CH:6]=1)=[O:4].[CH3:24][O:25]C(C1C(NC2C=CC(Br)=CC=2)=C(Cl)C2N=CNC=2C=1)=O.C1C(=O)[N:50](Cl)C(=O)C1.Cl.[C:55](=[O:58])(O)[O-].[Na+].OS([O-])=O.[Na+].[CH3:65][N:66]([CH:68]=O)[CH3:67]>O>[OH:25][CH2:24][CH2:55][O:58][NH:50][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:8]2[N:9]=[CH:68][N:66]([CH3:65])[C:67]=2[CH:6]=1)=[O:4]

参加物

9

反応物 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 31398Chlorosuccinimide2 回HCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 668983426-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl esterHCID 688177756-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester

生成物 1

HCID 588906256-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide収率 57%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester 10dd: 6-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester 8g (0.225 g, 0.591 mmol) is dissolved in DMF (2 mL) and NCS (79 mg, 0.591 mmol) is added. After the NCS is in solution concentrated HCl (0.005 mL, 0.059 mmol) is added. After 2 hours, sodium bicarbonate, water and NaHSO3 are added to the reaction mixture. Solids are filtered and washed with water and ether to give 0.141 g (57%) of clean desired product as a tan solid. MS APCI (−) m/z 414, 416 (M−, Br pattern) detected.

後処理

  1. additionis added
  2. filtrationSolids are filtered
  3. washwashed with water and ether

出典と根拠

ORDレコード
ord-f2ef374593604bbe82d04f779e7acbf0
出典データセット
uspto-grants-2012_06
特許番号
US08193231B2

反応ノート

読み込み中…