Trimethyl orthoformate → HCID 72742603, compound

HRID 1607842Notes

Reaction equation

HRID 1607842 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][NH:6][CH2:7][CH:8]=[CH2:9])[CH3:2].[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1)=O.Cl.[NH2:24][OH:25].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:25][N:24]=[C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:6]([CH2:7][CH:8]=[CH2:9])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])=[O:22])=[CH:16][CH:15]=1)[CH3:11]

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 994524-Acetylphenyl isocyanateHCID 443297Hydroxyamine hydrochlorideHCID 10975597N-2-Propen-1-ylglycine ethyl ester

Product 1

HCID 72742603HCID 72742603, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.02 mol N-allylglycine ethyl ester, prepared as described byS. B. Hyeon, I. Nagai, H. Tesaka, T. Kajita, and M. Furushima in European Patent Application No. 181,494, in 40 mL of THF is added dropwise to a solution of 0.02 mol of 4-isocyanatoacetophenone, prepared as described byE. E. Kilbourn, D. L. Peardon, and J. E. Ware in U.S. Pat. No. 3,931,203, 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 residueis 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 byrotary evaporator to give the product, N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyl-N'-ethoxycarbonylmethylurea.

Workup

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

Sources & evidence

ORD record
ord-a1783882885d494fa158f1b827db64e3
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

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