Hydrochloric Acid → HCID 178521995, compound

HRID 1609292Notes

Reaction equation

HRID 1609292 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:35])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:20][CH:19]=1)#[N:2].[N-:36]=[N+:37]=[N-:38].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[NH:36]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:35])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:20][CH:19]=2)=[N:2][N:38]=[N:37]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 20084456HCID 20084456, compound

Product 1

HCID 178521995HCID 178521995, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of DMF were dissolved 1.35 g of N-[2-(2-cyanophenylthio)phenyl]-4-(4-phenylbutoxy)benzamide, 0.55 g of sodium azide and 0.46 g of ammonium chloride, and the mixture was stirred at 110°-115° C. for 5 hours. Then, 0.18 g of sodium azide and 0.15 g of ammonium chloride were further added and the mixture was stirred at 110° to 115° C. for 2 hours. After addition of ice-water, the reaction mixture was neutralized with diluted hydrochloric acid and the precipitate was collected by filtration and recrystallized from ethanol to give 0.95 g of the title compound, m.p. 156°-159° C.

Workup

  1. stirringthe mixture was stirred at 110° to 115° C. for 2 hours
  2. filtrationthe precipitate was collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bcc15aeeffda460f948815d5ec91170e
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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