Ammonia → Aclonifen

HRID 1902593Notes

Reaction equation

HRID 1902593 reaction equation
[Cl:1][C:2]1[C:7](OC2C=CC=CC=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH3:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH2:25]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 128811472-Chloro-4-nitro-1,3-diphenoxy-benzene

Product 1

HCID 92389AclonifenYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

68.3 gm of 2-chloro-4-nitro-1,3-diphenoxy-benzene were dissolved in 300 ml of toluene, and the solution was admixed with 100 ml of concentrated aqueous ammonia in an autoclave. The autoclave was then closed, the internal pressure was increased to 3 bar with gaseous ammonia, and the contents were heated for 12 hours at 120° C., whereby the internal pressure rose to about 13 bar. Thereafter, the contents were allowed to cool, and the organic phase was separated, extracted with dilute hydrochloric acid, dried with sodium sulfate and the toluene was distilled off. The reaction product was obtained with virtually quantitative yield (54 gm). Gas-chromatographic analysis revealed that the reaction product contained 98% of the title compound, m.p. 81°-82° C.

Workup

  1. customThe autoclave was then closed
  2. temperatureto cool
  3. customthe organic phase was separated
  4. extractionextracted with dilute hydrochloric acid
  5. dry with materialdried with sodium sulfate
  6. distillationthe toluene was distilled off
  7. customThe reaction product was obtained with virtually quantitative yield (54 gm)

Sources & evidence

ORD record
ord-b8ee73217593426d8c13d5ea86758f38
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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