Dibromomethane → 4-(2-(5-bromo-4-(2-chloro-4-cyclopropyl-6-methylphenyl)-4H-1,2,4-triazol-3-ylthio)acetamido)-3-chlorobenzoic acid

HRID 889404

反応式

HRID 889404 の反応式
ClC(Cl)C(O)=O.N[C:8]1[N:9]([C:28]2[C:33]([CH3:34])=[CH:32][C:31]([CH:35]3[CH2:37][CH2:36]3)=[CH:30][C:29]=2[Cl:38])[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1.N([O-])=O.[Na+].ClCCl.[Br:46]CBr>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:46][C:8]1[N:9]([C:28]2[C:33]([CH3:34])=[CH:32][C:31]([CH:35]3[CH2:37][CH2:36]3)=[CH:30][C:29]=2[Cl:38])[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1

参加物

7

反応物 5

HCID 3024DibromomethaneHCID 6344DichloromethaneHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 598130994-(2-(5-amino-4-(2-chloro-4-cyclopropyl-6-methylphenyl)-4H-1,2,4-triazol-3-ylthio)acetamido)-3-chlorobenzoic acid

生成物 1

HCID 162218154-(2-(5-bromo-4-(2-chloro-4-cyclopropyl-6-methylphenyl)-4H-1,2,4-triazol-3-ylthio)acetamido)-3-chlorobenzoic acid収率 42%

試薬・触媒・溶媒 1

HCID 165294Benzyltriethylammonium bromide触媒

実験手順

Dichloroacetic acid (0.065 mL, 0.78 mmol) was added to a mixture of compound 6 (192 mg, 0.39 mmol), benzyltriethyl ammonium bromide (318 mg, 1.17 mmol) and sodium nitrite (538 mg, 7.8 mmol) in dibromomethane (10 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated and the resulting residue was purified by prep. TLC (95% dichloromethane/5% methanol) to afford 88 mg, 42% yield of 4-(2-(5-bromo-4-(2-chloro-4-cyclopropyl-6-methylphenyl)-4H-1,2,4-triazol-3-ylthio)acetamido)-3-chlorobenzoic acid (7).

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. customthe resulting residue was purified by prep

出典と根拠

ORDレコード
ord-8f5442b5fc924f86808779fe20c60690
出典データセット
uspto-grants-2012_08
特許番号
US08252828B2

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