Ammonia → HCID 19774727, compound

HRID 1614024Notes

Reaction equation

HRID 1614024 reaction equation
CO[C:3]1[C:4]([N+:34]([O-:36])=[O:35])=[C:5]([C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([NH:27][CH2:28][CH2:29][OH:30])[C:16]=2[N+:31]([O-:33])=[O:32])[C:6]([N+:12]([O-:14])=[O:13])=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[NH3:37]>CO>[NH2:37][C:7]1[C:6]([N+:12]([O-:14])=[O:13])=[C:5]([C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([NH:27][CH2:28][CH2:29][OH:30])[C:16]=2[N+:31]([O-:33])=[O:32])[C:4]([N+:34]([O-:36])=[O:35])=[CH:3][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 19774720HCID 19774720, compound

Product 1

HCID 19774727HCID 19774727, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 0.55 g (0.0011 mole) of 3-methoxy-3'-(2-hydroxyethylamino)-2,2',4,4',6,6'-hexanitrobiphenyl and 10 ml of methanol was stirred in an ice bath while a solution of gaseous ammonia in methanol was added until the mixture remained basic to damp pH paper. The mixture was then kept basic with ammonia as it was stirred at room temperature for 3 hours. After standing overnight, the insoluble yellow solid product 3-amino-3'-(2-hydroxyethylamino)-2,2',4,4',6,6'-hexanitrobiphenyl was removed to give 0.45 g (85%), mp 246° C. dec; 1H NMR (acetone-d6 +D2O): 3.28 (t, 2H), 3.90 (t, 2H), 9.50 (overlapping s, 2H).

Workup

  1. additionwas added until the mixture
  2. waitAfter standing overnight
  3. customthe insoluble yellow solid product 3-amino-3'-(2-hydroxyethylamino)-2,2',4,4',6,6'-hexanitrobiphenyl was removed
  4. customto give 0.45 g (85%), mp 246° C. dec

Sources & evidence

ORD record
ord-062d5e9881e84c8585b1fc6ae8866b2f
Source dataset
uspto-grants-1993_03
Patent number
US05194659

Reaction notes

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