Trimethyl orthoformate → HCID 72742603, compound

HRID 1111042Notes

Reaction equation

HRID 1111042 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 by S. B. Hyeon, I. Nagai, H. Iesaka, 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 by E. 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 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'-allyl-N'-ethoxycarbonylmethylurea.

Workup

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

Sources & evidence

ORD record
ord-d94d92bf8fcb4c2ca7cd96d94acd4e78
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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