Formamide → HCID 178484997, compound

HRID 330099Notes

Reaction equation

HRID 330099 reaction equation
C(O[CH:4]([C:16](=O)[CH3:17])[CH2:5][S:6][CH2:7][CH2:8][NH:9][C:10]([NH:13][C:14]#[N:15])=[N:11][CH3:12])=O.C([O-])([O-])OC.[CH:24]([NH2:26])=O.C([O-])=O.[NH4+:30]>>[CH3:17][C:16]1[NH:26][CH:24]=[N:30][C:4]=1[CH2:5][S:6][CH2:7][CH2:8]/[N:9]=[C:10](/[NH:13][C:14]#[N:15])\[NH:11][CH3:12]

Participants

5

Reactant 4

HCID 713FormamideHCID 2723923Ammonium formateHCID 14622764N-cyano-N'-[2-(2-formyloxy-3-oxobutylthio)ethyl]-N"-methylguanidineHCID 53629101Methylorthoformate

Product 1

HCID 178484997HCID 178484997, compoundYield 56%

Conditions

Temperature
100 °C

Procedure

136 mg of N-{2-(2-formyloxy-3-oxobutylthio)ethyl}-N'-cyano-N"-methylguanidine and 530 mg of methyl orthoformate were dissolved in 2.5 m; of formamide, and 320 mg of ammonium formate was added. The mixture was stirred at 100° C. for 2 hours. Formamide was evaporated from the reaction mixture under reduced pressure. The residue was chromatographed on a column of silica gel (eluent: chloroform/methanol=4/1), and then recrystallized from isopropanol to give 71 mg (yield 56%) of the desired product (Cimetidine) as white crystals.

Workup

  1. customFormamide was evaporated from the reaction mixture under reduced pressure
  2. customThe residue was chromatographed on a column of silica gel (eluent: chloroform/methanol=4/1)
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-b225c7d67cd84417b6419f7f2d2468fc
Source dataset
uspto-grants-1990_01
Patent number
US04894475

Reaction notes

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