HCID 73197827, compound → HCID 18364140, compound

HRID 381852Notes

Reaction equation

HRID 381852 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[N:20][OH:21])[CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH2:15][CH2:16][C:17](=[O:19])[O:21][N:20]=3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 73197827HCID 73197827, compound

Product 1

HCID 18364140HCID 18364140, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 4-(4′-chloro-biphenyl-4-yl)-4-hydroxyimino-butyric acid (2.126 g, 0.00700 mol) and 4-methylphenyl)sulfonic acid monohydrate (0.067 g, 0.00035 mol) in toluene (22 mL) was heated under nitrogen at reflux over a Dean-Stark trap for 7 hours, and allowed to cool. The volatiles were rotary evaporated. The residue was dissolved/suspended in dichloromethane and chromatographed on silica gel (221 g, 230-400 mesh), eluting with dichloromethane (20×200 mL) to give 0.63 g of 3-(4′-chloro-biphenyl-4-yl)-4,5-dihydro-6-oxo-6H-1,2-oxazine as a light purple solid; mp 190-192° C.

Workup

  1. temperaturewas heated under nitrogen
  2. temperatureat reflux over a Dean-Stark trap for 7 hours
  3. temperatureto cool
  4. customchromatographed on silica gel (221 g, 230-400 mesh)
  5. washeluting with dichloromethane (20×200 mL)

Sources & evidence

ORD record
ord-a7560ea0314a4505a46e271236b210ca
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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