1,1-Dimethylhydrazine → N-dimethylamino-3-chloro-2,6-dinitro-4-trifluoromethylaniline

HRID 971464Notes

Reaction equation

HRID 971464 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[CH3:19][N:20]([CH3:22])[NH2:21]>C1CCCCC1>[CH3:19][N:20]([CH3:22])[NH:21][C:6]1[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([C:15]([F:18])([F:17])[F:16])=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 13101276N-dimethylamino-3-chloro-2,6-dinitro-4-trifluoromethylanilineYield 85%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To 20.0 g. (0.065 mole) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 300 ml. of cyclohexane in a 500 ml. round-bottom flask equipped with a stirrer and dropping funnel was added 7.86 g. (0.13 mole) of 1,1-dimethylhydrazine at ambient temperature. The addition was drop-wise over a period of about 20 minutes. Stirring was continued for 22 hours at room temperature. The resultant mixture was filtered and the insoluble solid then stirred with 300 ml. of water for one hour to dissolve the hydrazine hydrochloride. The insoluble product was isolated by filtration and washed with water. Recrystallization from 95% ethanol gave 18.3 g. (85%) of the desired product as a yellow solid, m.p. 130°-131° C.

Workup

  1. customround-bottom flask equipped with a stirrer
  2. additionwas added 7.86 g
  3. customat ambient temperature
  4. additionThe addition
  5. waitwas continued for 22 hours at room temperature
  6. filtrationThe resultant mixture was filtered
  7. stirringthe insoluble solid then stirred with 300 ml
  8. dissolutionof water for one hour to dissolve the hydrazine hydrochloride
  9. customThe insoluble product was isolated by filtration
  10. washwashed with water
  11. customRecrystallization from 95% ethanol
  12. customgave 18.3 g

Sources & evidence

ORD record
ord-299abbb3ee0e4cf4978368271754ea3e
Source dataset
uspto-grants-1979_07
Patent number
US04160090

Reaction notes

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