Hydrochloric Acid → HCID 178505001, compound

HRID 1607696Notes

Reaction equation

HRID 1607696 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:5]([O:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH:4]=1)#[N:2].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[O:14][C:5]1[CH:4]=[C:3]([C:1]2[NH:25][N:24]=[N:23][N:2]=2)[CH:13]=[CH:12][C:6]=1[NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 10358871N-[4-cyano-2-(2,4-difluorophenoxy)phenyl]methanesulfonamide

Product 1

HCID 178505001HCID 178505001, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4'-cyano-2'-(2,4-difluorophenoxy)methanesulfonanilide (2.1 g), sodium azide (0.5 g) and ammonium chloride (0.43 g) in N,N-dimethylformamide (10 ml) was stirred for 6 hours at 110° C. The mixture was poured into a mixture of ice and diluted hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried and concentrated in vacuo. The residual crystals were recrystallized from ethyl acetate to give colorless crystals of 2'-(2,4-difluorophenoxy)-4'-(5-tetrazolyl)methanesulfonanilide (2.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residual crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cbf3f629030c428d8c405179edcf0277
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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