Acetic Acid → HCID 178507517, compound

HRID 1609282Notes

Reaction equation

HRID 1609282 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+].C(O)(=O)C>CN(C=O)C.O>[NH:17]1[C:11]([C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])=[N:12][N:19]=[N:18]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 3662332-(2-Aminophenyl)sulfanylbenzonitrile

Product 1

HCID 178507517HCID 178507517, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 25 ml of DMF were suspended 2.4 g of 2-(2-aminophenylthio)benzonitrile (prepared in accordance with Reference Example 5, Step 4), 3.4 g of sodium azide and 1.7 g of ammonium chloride and the suspension was stirred at 110°-120° C. for 5 hours. After cooling, the reaction mixture was diluted with water, acidified with acetic acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated and the residue was crystallized from ethyl acetate and isopropyl ether to give 1.9 g of the title compound as white crystals, m.p. 153°-156° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was crystallized from ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-43ac6c55903d4dd3a5b6d0b01679396f
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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