Phenylacetyl chloride → N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)benzene-acetamide

HRID 613078Notes

Reaction equation

HRID 613078 reaction equation
Cl.[NH2:2][C:3]1[C:4](=[O:16])[O:5][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:8]=1[OH:9].C(N(CC)CC)C.[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](Cl)=[O:32])=[CH:26][CH:25]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:9][C:8]1[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:16])[C:3]=1[NH:2][C:31](=[O:32])[CH2:30][C:27]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 546812893-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride

Product 1

HCID 54681362N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)benzene-acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method E using 3-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride (0.150 g, 0.626 mmol), methylene chloride (6 mL), triethylamine (0.348 mL, 2.50 mmol), catalytic 4-dimethylaminopyridine, phenacetyl chloride (0.106 g, 0.626 mmol). m.p. dec. 213° C.; 1H NMR (250 MHz, DMSO-d6) δ3.69 (s, 2 H), 6.85 (s, 1 H), 7.29 (m, 4 H), 7.53 (m, 3 H), 7.83 (m, 2 H), 9.40 (bs, 1 H).

Workup

  1. custom213° C.

Sources & evidence

ORD record
ord-55ec4556280447d79141222254e91307
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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