HCID 59264779, compound → HCID 59264804, compound

HRID 646526Notes

Reaction equation

HRID 646526 reaction equation
[C:1]([O:9][C:10]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:11]=1[C:12]([C:14]1([Br:22])[N:16]=[C:15]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[C:1]([O:9][C:10]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:11]=1[C:12]1[O:13][N:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:14]=1[Br:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 59264779HCID 59264779, compound

Product 1

HCID 59264804HCID 59264804, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 3-(2-benzoyloxy-5-chloro-benzoyl)-3-bromo-3H-azirine-2-carboxylate (55 mg, 0.12 mmol) was heated at reflux in dry toluene for 2 hours. After evaporation of the solvent, crude solids (34 mg) were obtained and purified by preparative TLC (EtOAc:hexane/1:2). Rf=0.73 (fluorescent). 1H NMR (d6-acetone) δ=7.60 (1H, d); 7.50 (1H, dd); 7.40 (1H, d); 7.30 (5H, m); 5.25 (2H, s); 4.42 (2H, q) and 1.40 (3H, t). LCMS: (M+1)+=438.0 (RT=7.09 min.)

Workup

  1. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-cb12df052c734c15aba18a2776482f3b
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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