Pyridine → HCID 73867328, compound

HRID 1111043Notes

Reaction equation

HRID 1111043 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][NH:6][CH2:7][CH:8]=[CH:9][CH3:10])[CH3:2].N([CH2:15][CH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)=C=O.Cl.[NH2:27][OH:28].C([O:34][CH3:35])(OC)OC.[N:36]1C=CC=CC=1>C1COCC1>[OH:28][N:27]=[C:18]([C:20]1[CH:21]=[CH:22][C:23]([NH:36][C:35]([N:6]([CH2:7][CH:8]=[CH:9][CH3:10])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:11])=[O:34])=[CH:24][CH:25]=1)[CH2:17][CH2:16][CH3:15]

Participants

7

Reactant 5

HCID 1049PyridineHCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 22154871HCID 22154871, compoundHCID 53851665HCID 53851665, compound

Product 1

HCID 73867328HCID 73867328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.02 mol N-2-butenylglycine 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-isocyanatobutyrophenone, 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-hydroxyiminobutyl)phenyl]-N'-(2-butenyl)-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-513c85448db748bcbd000c144049db03
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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