1-Methylhydantoin → HCID 67787144, compound

HRID 1648508Notes

Reaction equation

HRID 1648508 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=2)[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:23][N:24]1[CH2:30][C:28](=[O:29])[NH:27][C:25]1=[O:26]>>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][CH:18]=2)[C:7](/[CH:10]=[C:30]2/[N:24]([CH3:23])[C:25](=[O:26])[NH:27][C:28]/2=[O:29])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 692171-MethylhydantoinHCID 10334966Methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-YL)methyl]benzoate

Product 1

HCID 67787144HCID 67787144, compound

Procedure

This compound is prepared by a procedure similar to Example 1 except that the starting materials are the ester derivative, 2-butyl-1-(4-carbomethoxybenzyl)-5-formylimidazole, and 1-methylhydantoin. The crude mixed isomer products are purified and separated by silica gel column chromatography, eluting with 0.1:1.5:10 glacial acetic acid-methanol-chloroform. The "slow" moving material is the (E) isomer; tlc (0.1:2:10 acetic acid-methanol-chloroform system) 1 spot, Rf 0.5; mp 219°-221° C.; nmr (DMSO-d6), vinyl proton at δ 5.96 ppm; MS (CI) 383 (M39 +1).

Workup

  1. customThis compound is prepared by a procedure similar to Example 1 except that the starting materials
  2. additionThe crude mixed isomer products
  3. customare purified
  4. customseparated by silica gel column chromatography
  5. washeluting with 0.1:1.5:10 glacial acetic acid-methanol-chloroform

Sources & evidence

ORD record
ord-57f688a10a844c599f7f93f1897953f5
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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