Ammonia → HCID 57045220, compound

HRID 917884Notes

Reaction equation

HRID 917884 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([C:13]#[N:14])=[C:6](Cl)[C:5]=1[N+:16]([O-:18])=[O:17])[CH3:2].[NH3:21].C(COC)OC>C(O)C>[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]1[C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH2:21])[C:7]([C:13]#[N:14])=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 80711,2-DimethoxyethaneHCID 21524229HCID 21524229, compound

Product 1

HCID 57045220HCID 57045220, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.33 g. (0.0144 mole) of N,N-diethyl-3-chloro-2,6-dinitro-4-cyanoaniline, 6.40 g. (0.0288 mole) of a 7.66% solution of ammonia in absolute ethanol, and 15 ml. of dimethoxyethane was sealed in a Pyrex reaction tube and alloed to stand at room temperature for 72 hours. The contents were distilled to dryness at reduced pressure and extracted with 100 ml. of boiling chloroform. The filtered chloroform extract was evaporated to dryness and the residual orange solid taken up in hot 95% ethanol. Upon cooling, the product crystallized and was isolated by filtration to give 1.51 g. (37.3%) or an orange, crystalline solid melting at 142°-145°C. Recrystallization from 95% ethanol gave the desired product, m.p. 145.5°-146.5°C.

Workup

  1. distillationThe contents were distilled to dryness at reduced pressure
  2. extractionextracted with 100 ml
  3. extractionThe filtered chloroform extract
  4. customwas evaporated to dryness
  5. temperatureUpon cooling
  6. customthe product crystallized
  7. customwas isolated by filtration
  8. customto give 1.51 g
  9. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-6d70745ee88c48d4a4751f83ec4461d4
Source dataset
uspto-grants-1976_07
Patent number
US03968138

Reaction notes

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