Ethylene Glycol → HCID 22819139, compound

HRID 1902445Notes

Reaction equation

[O:1]=[C:2]1[N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:6]2=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=[CH:14][N:5]2[C:4]2[CH:20]=[CH:21][S:22][C:3]1=2.[C-]#N.[K+].C(O)C[OH:28]>>[O:1]=[C:2]1[N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:6]2=[C:12]([C:15]([O:17][CH2:18][CH2:19][OH:28])=[O:16])[N:13]=[CH:14][N:5]2[C:4]2[CH:20]=[CH:21][S:22][C:3]1=2

Participants

Reactant 3

HCID 174Ethylene Glycol

HCID 9032Potassium Cyanide

HCID 13688160ethyl (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylate

Product 1

HCID 22819139HCID 22819139, compound

Conditions

Temperature: 100 °C

Procedure

A mixture of 3.12 g (10 mmol) of ethyl (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylate, 80 mg of powdered potassium cyanide and 30 ml of ethyleneglycol is stirred at 100° C. overnight. After removal of the ethyleneglycol, the residue is purified by column chromatography. There is obtained 2-hydroxyethyl (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylate of melting point 182°-185° C.

Workup

customAfter removal of the ethyleneglycol
customthe residue is purified by column chromatography

Sources & evidence

ORD record: ord-37b15504ff554fb992e1a2c31402efb6
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04363762

Reaction notes

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