Ammonium Chloride → HCID 178419799, compound

HRID 1731627Notes

Reaction equation

HRID 1731627 reaction equation
[CH2:1]1[C:20]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]#[N:18])[CH:15]=[CH:16][C:10]=4[CH:9]=[CH:8][C:7]=3[CH:19]=2)[CH2:3][CH2:2]1.[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[CH2:1]1[C:20]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]5[NH:23][N:22]=[N:21][N:18]=5)[CH:15]=[CH:16][C:10]=4[CH:9]=[CH:8][C:7]=3[CH:19]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 25517Ammonium Chloride3×HCID 33557Sodium Azide3×HCID 13746697HCID 13746697, compound

Product 1

HCID 178419799HCID 178419799, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,3-dihydro-1H-benzo[b]indeno[5,6-f]thiepin-7-carbonitrile (2.10 g, 7.625 mmole) in dimethylformamide (31.5 ml) stirred under reflux (oil-bath at 170°-180° C.) in an atmosphere of argon was treated with a mixture of sodium azide (743 mg, 11.44 mmole) and ammonium chloride (612 mg, 11.44 mmole). An equal portion of sodium azide and ammonium chloride was added after 1 hour and then at 30 minute intervals seven portions of a mixture of sodium azide (247 mg, 3.81 mmole) and ammonium chloride (204 mg, 391 mmole) were added. After heating for a further 1 hour the reaction mixture was allowed to cool, then it was diluted with water (150 ml) and acidified. An extraction with methylene chloride (250 ml) was performed. The methylene chloride solution was extracted with a mixture of water (100 ml) and 5N sodium hydroxide (10 ml) and after a further wash with water the combined aqueous extract on acidification yields 1.555 g of title compound.

Workup

  1. temperatureunder reflux (oil-bath at 170°-180° C.) in an atmosphere of argon
  2. additionwere added
  3. temperatureAfter heating for a further 1 hour the reaction mixture
  4. temperatureto cool
  5. extractionAn extraction with methylene chloride (250 ml)
  6. extractionThe methylene chloride solution was extracted with a mixture of water (100 ml) and 5N sodium hydroxide (10 ml)
  7. washafter a further wash with water the combined
  8. extractionaqueous extract on acidification

Sources & evidence

ORD record
ord-7f43557538c443c3897a7a5072a899df
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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