Dimethyl Sulfoxide → HCID 70407844, compound

HRID 569076Notes

Reaction equation

HRID 569076 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](C)[C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15](Br)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.O.[CH3:30]S(C)=O>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:30][C:25]1[NH:24][CH:28]=[CH:27][N:26]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 962WaterHCID 70407463HCID 70407463, compound

Product 1

HCID 70407844HCID 70407844, compound

Procedure

5-Bromo-methyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester (0.35 g) is left with imidazole (0.13 g) in dimethyl sulfoxide (4 ml) for three days at room temperature. The precipitate resulting after addition of water (40 ml) is recrystallized from ethanol and chromatographed on silica gel with a mixture of 19 parts of dichloromethane and one part of methanol. Thus 0.2 g of 5-(1-imidazolylmethyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester with a melting point of 220°-222° C. is obtained.

Workup

  1. customThe precipitate resulting
  2. customis recrystallized from ethanol
  3. customchromatographed on silica gel with a mixture of 19 parts of dichloromethane and one part of methanol

Sources & evidence

ORD record
ord-8305251aab49413dbab90f4c55380b8c
Source dataset
uspto-grants-1988_03
Patent number
US04731365

Reaction notes

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