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

HRID 425301
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HRID 425301 반응식
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
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참가 물질

7

반응물 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

생성물 1

HCID 16221815
4-(2-(5-bromo-4-(2-chloro-4-cyclopropyl-6-methylphenyl)-4H-1,2,4-triazol-3-ylthio)acetamido)-3-chlorobenzoic acid
수율 42%

시약·촉매·용매 1

HCID 165294Benzyltriethylammonium bromide촉매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-34b2aeaf6a7848afbea8322cbaa284f3
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106205B2

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