Ammonia methanol → HCID 178441019, compound

HRID 2105258Notes

Reaction equation

HRID 2105258 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9](SC)[NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[NH3:28].CO>>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[NH:28])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 178503860HCID 178503860, compound

Product 1

HCID 178441019HCID 178441019, compoundYield 46%

Conditions

Temperature
40 °C

Procedure

A solution of methyl N′-(3-fluorophenyl)-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]carbamimidothioate (0.0094 mol) in NH3/CH3OH (60 ml) was stirred and heated in autoclave at 40° C. for 3 days. The solvent was evaporated and the residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.2 to 90.10/0.5). The pure fractions were collected and evaporated. The residue was crystallized from 2-propanone and (C2H5)2O and filtered off, yielding 0.89 g (46%) N′-(3-fluorophenyl)-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]guanidine (compound 744).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.2 to 90.10/0.5)
  3. customThe pure fractions were collected
  4. customevaporated
  5. customThe residue was crystallized from 2-propanone and (C2H5)2O
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-fb50b46ced8c4174ab66653297de7498
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

Loading…