Formamide → HCID 178484998, compound

HRID 477286Notes

Reaction equation

HRID 477286 reaction equation
[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12](=O)[CH:13]([NH:15][CH:16]=O)[CH3:14])=[N:5][CH3:6])#[N:2].C([O-])=O.[NH4+].C([O-])([O-])OC.O.O.O.O.P([O-])([O-])(O)=O.[NH4+].[Na+].C([NH2:41])=O>>[C:1]([NH:3][C:4]([NH:5][CH3:6])=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[N:41]=[CH:16][NH:15][C:13]=1[CH3:14])#[N:2]

Participants

6

Reactant 5

HCID 713FormamideHCID 2723923Ammonium formateHCID 14457222N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidineHCID 53629101MethylorthoformateHCID 56924540Ammonium sodium phosphate tetrahydrate

Product 1

HCID 178484998HCID 178484998, compoundYield 87%

Conditions

Temperature
100 °C

Procedure

To 136 mg of N-cyano-N'-[2-(3-formylamino-2-oxobutylthio)ethyl]-N"-methylguanidine, 320 mg of amonium formate, 0.6 ml of methyl orthoformate and 209 mg of sodium ammonium hydrogenphosphate tetrahydrate was added 2.5 ml of formamide, and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled and insoluble substances were removed, and the solvent was removed under reduced pressure and the obtained residue was refined by silica gel column chromatography (eluting solvent: chloroform/ethanol=5/1) and recrystallized from isopropanol/ether (60/40) to obtain 100 mg of intended Cimetidine (the yield was 87%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custominsoluble substances were removed
  3. customthe solvent was removed under reduced pressure
  4. washthe obtained residue was refined by silica gel column chromatography (eluting solvent: chloroform/ethanol=5/1)
  5. customrecrystallized from isopropanol/ether (60/40)

Sources & evidence

ORD record
ord-d8c756f6edd649dda9bd58fd304200f5
Source dataset
uspto-grants-1989_12
Patent number
US04886910

Reaction notes

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