Methyl Isocyanate → HCID 13269218, compound

HRID 2412426Notes

Reaction equation

HRID 2412426 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[C:9]([NH:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[O:17][C:18]([CH2:21][N:22]([CH3:24])[CH3:23])=[CH:19][CH:20]=1)=[O:10]>C(O)C>[CH3:1][NH:2][C:3](=[O:4])[NH:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[C:9]([NH:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[O:17][C:18]([CH2:21][N:22]([CH3:23])[CH3:24])=[CH:19][CH:20]=1)=[O:10]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 13269217HCID 13269217, compound

Product 1

HCID 13269218HCID 13269218, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 2.3 g of methyl isocyanate in 10 ml of absolute ethanol is added dropwise to a solution of 6 g of 3-amino-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide in 50 ml of absolute ethanol. Then the mixture is left to stand 30 minutes at room temperature and afterwards it is heated at 50° C. for 2 hours. The solvent is evaporated under reduced pressure, the residue is taken up with diluted hydrochloric acid, the aqueous solution is extracted twice with 100 ml of ethyl acetate and treated with concentrated sodium hydroxide to clearly basic pH. The mixture is extracted three times with 100 ml of ethyl acetate, the organic phase is washed with water, dried on anhydrous sodium sulfate and evaporated to dryness. Thus, the 3-(3-methylureido)-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide is obtained as an oil which is dissolved in isopropanol and treated with a solution of 1.5 g of oxalic acid in isopropanol. A white solid is obtained which, after crystallization from 95% ethanol gives 4.5 g of 3-(3-methylureido)-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide oxalate; m.p. 156°-158° C. Code number: SR 57934A.

Workup

  1. waitThen the mixture is left
  2. customThe solvent is evaporated under reduced pressure
  3. extractionthe aqueous solution is extracted twice with 100 ml of ethyl acetate
  4. additiontreated with concentrated sodium hydroxide to clearly basic pH
  5. extractionThe mixture is extracted three times with 100 ml of ethyl acetate
  6. washthe organic phase is washed with water
  7. dry with materialdried on anhydrous sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-01f7425ae3f64812987628a3de880816
Source dataset
uspto-grants-1985_01
Patent number
US04492711

Reaction notes

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