3-Phenoxyaniline → HCID 22118339, compound

HRID 1274873Notes

Reaction equation

HRID 1274873 reaction equation
[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:14])([CH3:13])[C:9](=[O:12])[CH:10]=[CH2:11])[C:4](=[O:15])[C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O:22]([C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[O:22]([C:29]1[CH:30]=[C:31]([NH:32][CH2:11][CH2:10][C:9](=[O:12])[C:8]([N:5]2[C:4](=[O:15])[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:2]([CH3:1])[O:7][CH2:6]2)([CH3:13])[CH3:14])[CH:33]=[CH:34][CH:35]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 771353-PhenoxyanilineHCID 22118297HCID 22118297, compound

Product 1

HCID 22118339HCID 22118339, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-4-methylpent-1-en-3-one (50 mg), 3-phenoxyaniline (30 mg) and pyridine (0.2 ml) was heated at 40° C. for 1 hour then stirred overnight at 20° C. and at 40° C. for 4 hours. After evaporation the residue was purified by silica gel column chromatography eluting with isohexane/ethyl acetate to give 5-(3-phenoxyphenyl)amino-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpentan-3-one (Compound 1082, 69 mg), NMR 1.4(s,6H), 1.9(s,3H), 2.8(m,2H), 3.4(m,2H), 5.3(s,2H), 6.3-6.4(m,3H), 6.9-7.4(m,11H).

Workup

  1. customAfter evaporation the residue
  2. customwas purified by silica gel column chromatography
  3. washeluting with isohexane/ethyl acetate

Sources & evidence

ORD record
ord-f470e2a9e4d842df9353875fc55b9c66
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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