Trimethyl orthoformate → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonyl-N'methoxycarbonylmethylurea

HRID 1111051Notes

Reaction equation

HRID 1111051 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][NH:5][C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7].[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1)=O.Cl.[NH2:26][OH:27].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:27][N:26]=[C:14]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])[CH2:4][C:3]([O:2][CH3:1])=[O:12])=[O:24])=[CH:18][CH:17]=1)[CH3:13]

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 994524-Acetylphenyl isocyanateHCID 443297Hydroxyamine hydrochlorideHCID 22154858N-(allyloxycarbonyl)glycine methyl ester

Product 1

HCID 88615056N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonyl-N'methoxycarbonylmethylurea

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.02 mol N-(allyloxycarbonyl)glycine methyl ester in 40 mL of THF is added dropwise to a solution of 0.02 mol of 4isocyanatoacetophenone and 5 mL of pyridine in 40 mL of THF, and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL of CH3OH, and 0.022 mol of hydroxylamine hydrochloride and 0.06 mol of trimethyl orthoformate are added. The reaction mixture is heated to reflux for 1 hour. The solvent is removed by rotary evaporator to give the product, N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonyl-N'methoxycarbonylmethylurea.

Workup

  1. customThe solvent is then removed by rotary evaporator
  2. additionThe residue is dispersed in 50 mL of CH3OH
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux for 1 hour
  5. customThe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-7f058bf69e014a47be843a728a5526d1
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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