Hydrochloric Acid → 4-Chlorophenyl Isocyanate

HRID 262065

Reaction equation

HRID 262065 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](N)=[O:10])=[CH:4][CH:3]=1.N([O-])=O.[Na+].Cl.C(Cl)(Cl)Cl>O.F[B-](F)(F)F.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 87964-ChlorophenylureaHCID 23668193Sodium Nitrite

Product 1

HCID 76934-Chlorophenyl Isocyanate

Reagents, catalysts & solvents 2

HCID 67932Tetrabutylammonium TetrafluoroborateCatalystHCID 962WaterSolvent

Procedure

4-Chlorophenyl urea (8.5 parts) and a solution of sodium nitrite (6.9 parts) in water (10 parts) were added over 6 hours to a mixture of conc. hydrochloric acid (10.3 parts) chloroform (130 parts) and tetra-n-butyl ammonium fluoroborate (10% by weight based on 4-chlorophenyl urea) at -10° to -5° C. The mixture was stirred for a further 15 minutes then the stirrer stopped and layers allowed to separate. No solid was present at this stage. 5 mls of the organic layer was taken for analysis and the remainder kept cold until required.

Workup

  1. customto separate

Sources & evidence

ORD record
ord-b62cc6b7e3f94970b45c84cfc794cd41
Source dataset
uspto-grants-1979_05
Patent number
US04153624

Linked notes

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