Ammonium Chloride → HCID 178527341, compound

HRID 371513Notes

Reaction equation

HRID 371513 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:20]=[CH:19][C:14]([NH:15][CH2:16][C:17]#[N:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+]>[Cl-].[Li+].CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:20]=[CH:19][C:14]([NH:15][CH2:16][C:17]3[NH:23][N:22]=[N:21][N:18]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13478046HCID 13478046, compound

Product 1

HCID 178527341HCID 178527341, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 433294Lithium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A reaction mixture comprising 6.14 g of [p-(p-chlorophenylsulfonyl)anilino]acetonitrile, 1.43 g of sodium azide, 30 mg of lithium chloride, 1.18 g of ammonium chloride and 10 ml of dimethylformamide was stirred at 90° C. for 34 hours and then filtered. The solvent was removed in vacuo, the residue suspended in 50 ml of water and acidified with hydrochloric acid to pH2. The resulting solid was collected and recrystallized from acetic acid, giving 5.4 g of the desired product as tan crystals, mp 102°-105° C.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed in vacuo
  3. customThe resulting solid was collected
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-6e7d89eae70a448a8bdb4c4ed317d42b
Source dataset
uspto-grants-1985_07
Patent number
US04532349

Reaction notes

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