Methanol → 6-(1H-imidazol-1-ylmethyl)-2,3(1H,4H)-quinoxalinedione

HRID 1086220Notes

Reaction equation

HRID 1086220 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(C[C:18]([CH2:21]C)([O-])[O-:19])C.C[OH:24]>>[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]3[C:10](=[CH:11][CH:12]=2)[NH:13][C:18](=[O:19])[C:21](=[O:24])[NH:14]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 145184334-(1H-imidazol-1-ylmethyl)-1,2-benzenediamineHCID 86744885Diethyl ethanedioiate

Product 1

HCID 198758836-(1H-imidazol-1-ylmethyl)-2,3(1H,4H)-quinoxalinedioneYield 62.3%

Procedure

A mixture of 5 parts of 4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 4 parts of diethyl ethanedioiate and 40 parts of methanol was stirred for 4 hours at room temperature. The precipitated product was filtered off and dried, yielding 4 parts (62.3%) of 6-(1H-imidazol-1-ylmethyl)-2,3(1H,4H)-quinoxalinedione; mp. >300° C. (comp. 315).

Workup

  1. filtrationThe precipitated product was filtered off
  2. customdried

Sources & evidence

ORD record
ord-b0262b3975464f4397544f32995ea400
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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