Ammonium Hydroxide → HCID 61129737, compound

HRID 1484442Notes

Reaction equation

HRID 1484442 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:15](Cl)(=[O:17])=[O:16])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].[OH-].[NH4+:20]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([S:15](=[O:17])(=[O:16])[NH2:20])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 581587063-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride

Product 1

HCID 61129737HCID 61129737, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

16.2 g (1 mol equiv.) 3-Bromo-4-(2,2,2-trifluoro-acetylamino)-benzenesulfonyl chloride was dissolved in 150 mL acetonitrile and cooled to 0° C. Dropwise, 20.8 mL (3 mol equiv.) ammoniumhydroxide was added and the reaction mixture was stirred at room temperature for 10 min. during which a white precipitate was formed. Volatiles were removed under reduced pressure, and the solid residue was washed with water and dried in vacuo to afford 14.3 g (94%) N-(2-bromo-4-sulfamoyl-phenyl)-2,2,2-trifluoro-acetamide. 1H NMR (400 MHz, DMSO-d6) δ 7.59 (s, 2H), 7.69 (d, J=8.2 Hz, 1H), 7.88 (dd, J=8.2, 1.8 Hz, 1H), 8.14 (d, J=1.8 Hz, 1H), 11.55 (s, 1H).

Workup

  1. customwas formed
  2. customVolatiles were removed under reduced pressure
  3. washthe solid residue was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5c8c5523edb04d7fac5f4d69cf8d235c
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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