Acetic Acid → HCID 178502013, compound

HRID 437797Notes

Reaction equation

HRID 437797 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][O:6][C:5]([C:14]2[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.[C:23](=O)([O-])[NH2:24].[C:27]([OH:30])(=[O:29])C.Cl[CH:32](Cl)Cl>>[CH3:1][C:2]1([CH3:22])[CH2:3][O:4][C:5]([C:14]2[CH:19]=[CH:18][C:17]3[NH:20][C:23]([NH:24][C:27](=[O:29])[O:30][CH3:32])=[N:21][C:16]=3[CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:6][CH2:7]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 276CarbamateHCID 6212ChloroformHCID 21427081HCID 21427081, compound

Product 1

HCID 178502013HCID 178502013, compoundYield 48.5%

Procedure

A solution of 6 parts of 4-(5,5-dimethyl-2-phenyl-1,3-dioxan-2yl)-1,2-benzenediamine, 4.95 parts of methyl [(methylcarbonylamino)(methylthio)methylene[carbamate and 5 parts of acetic acid in 300 parts of trichloromethane is stirred and refluxed for 24 hours. The reaction mixture is evaporated and the residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 3.7 parts (48.5%) of methyl [5-(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)-1H-benzimidazol-2-yl]carbamate; mp. 224.5° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and 5% of methanol as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated

Sources & evidence

ORD record
ord-fd17164bd5024b6e8992db7c50a11532
Source dataset
uspto-grants-1977_06
Patent number
US04032536

Reaction notes

Loading…