Ethanolamine → HCID 57270951, compound

HRID 1090340Notes

Reaction equation

HRID 1090340 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].CO[C:7]1[C:8]([N+:41]([O-:43])=[O:42])=[C:9]([C:19]2[O:20][C:21]([C:24]3[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][C:27]([N+:33]([O-:35])=[O:34])=[C:26](OC)[C:25]=3[N+:38]([O-:40])=[O:39])=[N:22][N:23]=2)[C:10]([N+:16]([O-:18])=[O:17])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]>CO>[OH:2][CH2:1][CH2:3][NH:4][C:28]1[C:29]([N+:30]([O-:32])=[O:31])=[C:24]([C:21]2[O:20][C:19]([C:9]3[C:10]([N+:16]([O-:18])=[O:17])=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:7]([NH:4][CH2:3][CH2:1][OH:2])[C:8]=3[N+:41]([O-:43])=[O:42])=[N:23][N:22]=2)[C:25]([N+:38]([O-:40])=[O:39])=[CH:26][C:27]=1[N+:33]([O-:35])=[O:34]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 123775822,5-Bis(3-methoxy-2,4,6-trinitrophenyl)-1,3,4-oxadiazole

Product 1

HCID 57270951HCID 57270951, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.3 g (0.0049 mole) of ethanolamine in 20 ml of methanol was stirred in an ice bath during the addition of 1.0 g (0.0018 mole) of 2,5-bis(3-methoxy-2,4,6-trinitrophenyl)-1,3,4-oxadiazole. After 10 min. at 0° C., the mixture was stirred at room temperature for 5 hr. before the crude product [1.1 9 (94%), mp 250° dec] was removed by filtration. Digestion with boiling acetone gave the purified product, as an insoluble yellow solid, mp 264° C. dec.; 1H NMR (DMSO-d6 +D2O): 3.22 (t, 4H), 3.70 (t, 4H), 9.32 (s, 2H); IR(KBr): 3700-3200 (OH and NH), 1610, 1625 (C=N), 1545, 1340 (NO2). Anal. Calcd. for C18H14N10O15 : C, 35.42; H, 2.31; N, 22.95. Found: C, 35.62; H, 2.30; N, 22.93.

Workup

  1. custombefore the crude product [1.1 9 (94%), mp 250° dec] was removed by filtration
  2. customDigestion with boiling acetone gave the purified product

Sources & evidence

ORD record
ord-ecf415608b1a4d69aa9d9adb2f68df18
Source dataset
uspto-grants-1992_01
Patent number
US05081255

Reaction notes

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