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

HRID 889404Notes

Reaction equation

HRID 889404 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 165294Benzyltriethylammonium bromideCatalyst

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8f5442b5fc924f86808779fe20c60690
Source dataset
uspto-grants-2012_08
Patent number
US08252828B2

Reaction notes

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