Methyl Isocyanate → HCID 73886749, compound

HRID 2184649Notes

Reaction equation

HRID 2184649 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH3:5][O:6][N:7]=[C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][OH:26])=[CH:16][C:11]=2[O:10][CH2:9]1>O1CCCC1>[CH3:5][O:6][N:7]=[C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:25]([OH:26])[C:3]([NH:2][CH3:1])=[O:4])=[CH:16][C:11]=2[O:10][CH2:9]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 86757391HCID 86757391, compound

Product 1

HCID 73886749HCID 73886749, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.38 g of methyl isocyanate was added to a solution of 2.0 g of N-[2-(3-methoxyimino-2,3-dihydro-benzofuran-6-yloxymethyl)phenyl]-N-hydroxyamine in 50 ml of tetrahydrofuran, and they were stirred at room temperature for 8 hours. The reaction liquid was concentrated under reduced pressure to obtain 2.3 g of N-[2-(3-methoxyimino-2,3-dihydro-benzofuran-6-yloxymethyl)phenyl]-N-hydroxy-N′-methylurea. This product was dissolved in 20 ml of N,N-dimethylformamide. 0.95 g of methyl iodide and 0.98 g of anhydrous potassium carbonate were added to the solution, and they were stirred at room temperature for 4 hours. The reaction solution was diluted with 200 ml of diethyl ether, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate) to obtain 1.4 g of the title compound (having a m.p. of 109-112° C. and 1H-NMR data shown in the following table].

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9fa4075f46da48778ba2998834be6c51
Source dataset
uspto-grants-2002_06
Patent number
US06399542B1

Reaction notes

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