Methyl Isocyanate → N-(4-benzyloxybenzyl)-O-methylcarbamoylacetohydroxamic acid

HRID 1087639Notes

Reaction equation

HRID 1087639 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][N:14]([C:16](=[O:18])[CH3:17])[OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][N:22]=[C:23]=[O:24]>N12CCCN=C1CCCCC2.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][N:14]([C:16](=[O:18])[CH3:17])[O:15][C:23](=[O:24])[NH:22][CH3:21])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 129265N-(4-benzyloxybenzyl)acetohydroxamic acid

Product 1

HCID 15670601N-(4-benzyloxybenzyl)-O-methylcarbamoylacetohydroxamic acidYield 82.6%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-benzyloxybenzyl)acetohydroxamic acid (1.35 g), methyl isocyanate (0.65 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene catalyst (1 drop) in tetrahydrofuran (10 ml) was stirred for 3 hours then left overnight to provide N-(4-benzyloxybenzyl)-O-methylcarbamoylacetohydroxamic acid (1.35 g) m.pt. 101°-102° [from ethyl acetate-light petroleum (b.pt. 60°-80°)].

Workup

  1. waitthen left overnight

Sources & evidence

ORD record
ord-a7f6db8958e24b228d335a3f5db664a9
Source dataset
uspto-grants-1991_07
Patent number
US05036157

Reaction notes

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