Hydrochloric Acid → HCID 178501778, compound

HRID 1609293Notes

Reaction equation

HRID 1609293 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]([C:19]1[CH:30]=[CH:29][C:22]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1)=[O:18])#[N:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O.C(Cl)(Cl)Cl>[NH:31]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]([C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)=[O:18])=[N:2][N:33]=[N:32]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20084540HCID 20084540, compound

Product 1

HCID 178501778HCID 178501778, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

In 10 ml of DMF were suspended 1.1 g of methyl 4-[2-(2-cyanophenylthio)phenylcarbamoyl]phenoxyacetate, 0.85 g of sodium azide and 0.7 g of ammonium chloride, and the mixture was Stirred at 110°-120° C. for 8 hours. After cooling, the reaction mixture was acidified with concentrated hydrochloric acid and diluted with water. The resulting precipitate was subjected to silica gel column chromatography (chloroform→chloroform-ethanol=50:1) to give 0.4 g of the title compound as white crystals, m.p. 204°-205° C.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-4d928e8c79604675b4d715e987649454
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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