Dibromomethane → Rdea806

HRID 889408Notes

Reaction equation

HRID 889408 reaction equation
ClC(Cl)C(O)=O.N[C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([CH:38]3[CH2:40][CH2:39]3)=[CH:30][CH:29]=2)[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+].[Br:45]CBr>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:45][C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([CH:38]3[CH2:40][CH2:39]3)=[CH:30][CH:29]=2)[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

6

Reactant 4

HCID 3024DibromomethaneHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 573589664-[[2-[[5-amino-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl]thio]acetyl]amino]-3-chloroBenzoic acid

Product 1

HCID 16221816Rdea806Yield 34%

Reagents, catalysts & solvents 1

HCID 165294Benzyltriethylammonium bromideCatalyst

Procedure

Dichloroacetic acid (0.35 mL, 4.2 mmol) was added to a mixture of compound 6 (1.04 g, 2.1 mmol), benzyltriethyl ammonium bromide (1.65 g, 6.1 mmol) and sodium nitrite (2.9 g, 42.1 mmol) in dibromomethane (44 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 column chromatography (95% dichloromethane/5% methanol) to afford 393 mg, 34% yield of 4-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-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 column chromatography (95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-ac1db6d9d32648828750c862f044013e
Source dataset
uspto-grants-2012_08
Patent number
US08252828B2

Reaction notes

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