Dibromomethane → 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-N-(2-chloro-4-sulfamoylphenyl)acetamide

HRID 448144Notes

Reaction equation

HRID 448144 reaction equation
ClC(Cl)C(O)=O.N[C:8]1[N:9]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([CH:39]3[CH2:41][CH2:40]3)=[CH:31][CH:30]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][C:19]=2[Cl:28])=[O:16])=[N:11][N:12]=1.N([O-])=O.[Na+].[Br:46]CBr>>[Br:46][C:8]1[N:9]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([CH:39]3[CH2:41][CH2:40]3)=[CH:31][CH:30]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][C:19]=2[Cl:28])=[O:16])=[N:11][N:12]=1

Participants

5

Reactant 4

HCID 3024DibromomethaneHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 597636572-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide

Product 1

HCID 115199512-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-N-(2-chloro-4-sulfamoylphenyl)acetamideYield 31%

Procedure

Dichloroacetic acid (180 uL, 2.2 mmol) was added to a suspension of 2-[5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide (0.59 g, 1.1 mmol), sodium nitrite (1.5 g, 22 mmol) and BTEABr (0.91 g, 3.3 mmol) in dibromomethane (30 mL). The reaction mixture was stirred at room temperature for 4 hours, then extracted with dichloromethane and sodium bicarbonate in water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 2-[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide (224 mg, 31%).

Workup

  1. extractionextracted with dichloromethane and sodium bicarbonate in water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c158d8aa0c834bc290800cbbfab9bf6d
Source dataset
uspto-grants-2013_07
Patent number
US08481581B2

Reaction notes

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