Phosgene → 7-(4-Chlorophenyl)-8-isopropyl-3H-chromeno[7,8-d]oxazole-2,6-dione

HRID 14470Notes

Reaction equation

HRID 14470 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([CH:13]([CH3:15])[CH3:14])[O:9]2)=[CH:4][CH:3]=1.[C:24](Cl)(Cl)=[O:25].C(N(CC)CC)C>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:7]2[C:6](=[O:23])[C:5]3[CH:4]=[CH:3][C:2]4[NH:1][C:24](=[O:25])[O:12][C:11]=4[C:10]=3[O:9][C:8]=2[CH:13]([CH3:14])[CH3:15])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 687013867-Amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

Product 1

HCID 687041447-(4-Chlorophenyl)-8-isopropyl-3H-chromeno[7,8-d]oxazole-2,6-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 7-amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one (0.0532 g, 0.16 mmol) in anhydrous methylene chloride (2 ml) is treated at room temperature with a 20% phosgene in toluene solution (0.08 ml). After 30 min, triethylamine (0.032 g, 0.045 ml, 0.32 mmol, 2 eq.) is added, and the reaction mixture is stirred at room temperature for 1 h, transferred to the head of an aminoalkylated silica gel column (Sepra NH2, 50 micrometer, Phenomenex) and purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 1% acetic acid in ethyl acetate) to afford the title compound.

Workup

  1. custompurified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 1% acetic acid in ethyl acetate)

Sources & evidence

ORD record
ord-aeb373e030da411089de0d94b52959b2
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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