Ammonia → HCID 86733660, compound

HRID 917880Notes

Reaction equation

HRID 917880 reaction equation
[CH3:1][CH2:2][CH:3]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([CH3:16])=[C:9](Cl)[C:8]=1[N+:18]([O-:20])=[O:19])[CH2:4][CH3:5].[NH3:21]>C(COC)OC>[CH3:1][CH2:2][CH:3]([NH:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]([NH2:21])[C:10]([CH3:16])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54003484HCID 54003484, compound

Product 1

HCID 86733660HCID 86733660, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
94 °C

Procedure

A mixture of 5.00 g. (0.0165 mole) of N-(3-pentyl)-3-chloro-2,6-dinitro-4-methylaniline and 30 ml. of dimethoxyethane was charged to a glass reaction tube. The tube was cooled, 5 ml. of anhydrous ammonia condensed into it, and the tube was then sealed. After heating for 5 hours at 94°C., the tube was opened and the reaction mixture was stripped of volatile material. The residue was taken up in 250 ml. of hot cyclohexane, the solution filtered while hot, then stripped to give an orange residue which was crystallized from 95% ethanol to give 1.02 g. of the desired product as orange needles, m.p. 157°-160.5°C. After recrystallization from 95% ethanol the product melts at 160°-161.5°C.

Workup

  1. additionA mixture of 5.00 g
  2. temperatureThe tube was cooled
  3. customthe tube was then sealed
  4. filtrationof hot cyclohexane, the solution filtered while hot,
  5. customto give an orange residue which
  6. customwas crystallized from 95% ethanol
  7. customto give 1.02 g

Sources & evidence

ORD record
ord-8ea6b03940c14fa6bdfce60df09d0ef5
Source dataset
uspto-grants-1976_07
Patent number
US03968138

Reaction notes

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