Hydrochloric Acid → HCID 178509643, compound

HRID 867200Notes

Reaction equation

HRID 867200 reaction equation
Cl[C:2]1([C:17]#[N:18])[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-:23].[NH4+].Cl>CN(C)C=O>[Cl:23][C:14]1[CH:15]=[CH:16][C:11]([S:10][C:4]2[CH:3]=[C:2]([C:17]3[NH:18][N:21]=[N:20][N:19]=3)[CH:9]=[CH:8][C:5]=2[C:6]#[N:7])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 70624363HCID 70624363, compound

Product 1

HCID 178509643HCID 178509643, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Chlorophenylthioterephthalonitrile (3.28 g), sodium azide (0.78 g), ammonium chloride (0.65g) and dimethylformamide (30 ml) were heated together on the steam bath for 16 hr. The mixture was cooled and poured into dilute hydrochloric acid. The oil which precipitated and solidified slowly was dissolved in sodium bicarbonate solution and the solution extracted with chloroform to remove unchanged starting material. Acidification of the aqueous solution precipitated 2-(p-Chlorphenylthio)-4-(5-tetrazolyl)benzonitrile, decomposes at 222° C.

Workup

  1. temperatureThe mixture was cooled
  2. customThe oil which precipitated
  3. dissolutionsolidified slowly was dissolved in sodium bicarbonate solution
  4. extractionthe solution extracted with chloroform
  5. customto remove unchanged
  6. customAcidification of the aqueous solution precipitated 2-(p-Chlorphenylthio)-4-(5-tetrazolyl)benzonitrile
  7. customdecomposes at 222° C.

Sources & evidence

ORD record
ord-14cdbb9474a64a8b985b25b781d4db5c
Source dataset
uspto-grants-1978_07
Patent number
US04103015

Reaction notes

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