Ethanolamine → HCID 56977860, compound

HRID 1090342Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].CO[C:7]1[C:8]([N+:45]([O-:47])=[O:46])=[C:9]([C:21]2[O:22][C:23]([C:26]3[C:31]([N+:32]([O-:34])=[O:33])=[C:30](OC)[C:29]([N+:37]([O-:39])=[O:38])=[C:28](OC)[C:27]=3[N+:42]([O-:44])=[O:43])=[N:24][N:25]=2)[C:10]([N+:18]([O-:20])=[O:19])=[C:11](OC)[C:12]=1[N+:13]([O-:15])=[O:14]>CO>[OH:2][CH2:1][CH2:3][NH:4][C:28]1[C:27]([N+:42]([O-:44])=[O:43])=[C:26]([C:23]2[O:22][C:21]([C:9]3[C:8]([N+:45]([O-:47])=[O:46])=[C:7]([NH:4][CH2:3][CH2:1][OH:2])[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([NH:4][CH2:3][CH2:1][OH:2])[C:10]=3[N+:18]([O-:20])=[O:19])=[N:25][N:24]=2)[C:31]([N+:32]([O-:34])=[O:33])=[C:30]([NH:4][CH2:3][CH2:1][OH:2])[C:29]=1[N+:37]([O-:39])=[O:38]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.65 g (0.0106 mole) of ethanolamine in 40 ml of methanol was stirred in an ice bath while 1.55 g (0.00253 mole) of 2,5-bis(3,5-dimethoxy-2,4,6-trinitrophenyl)-1,3,4-oxadiazole was added. After 1 hr. at 0° C., the mixture was stirred for 5 hr. at room temperature before the insoluble solid (1.6 g, mp 230° C. dec.) was removed. The product was dissolved in dimethyl sulfoxide and methanol was added to give 1.4 g (76%), mp 237° C., 1H NMR (DMSO-d6 +D2O): 3.12 (m, 8H), 3.63 (m, 8H). Anal. Calcd. for C22H24N12O17 : C, 36.27; H, 3.32; N, 23.07. Found: C, 36.61; H, 3.32; N, 23.13.

Workup

additionwas added
customat room temperature before the insoluble solid (1.6 g, mp 230° C. dec.) was removed
dissolutionThe product was dissolved in dimethyl sulfoxide
additionmethanol was added
customto give 1.4 g (76%), mp 237° C., 1H NMR (DMSO-d6 +D2O): 3.12 (m, 8H), 3.63 (m, 8H)

Sources & evidence

ORD record: ord-0c54696240194caa9beecd28c555ecc3
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081255

Reaction notes

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