HCID 69497460, compound → HCID 13040227, compound

HRID 1594497Notes

Reaction equation

HRID 1594497 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([O:17]C(=O)C(Cl)(Cl)Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=[O:2].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]([O:42]C(=O)C(Cl)(Cl)Cl)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N+:39]([O-])=[O:40])[CH:29]=[CH:30][CH:31]=1>C(#N)C>[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:17])=[O:2].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:32](=[O:42])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N:39]=[O:40])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 69497460HCID 69497460, compoundHCID 69497549HCID 69497549, compound

Product 2

HCID 13040227HCID 13040227, compoundHCID 86760584HCID 86760584, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A more powerful 100 W high pressure mercury arc lamp was initially used for the irradiation of α-phenyl-2-nitrobenzyltrichloroacetate (33) and α-(3-methoxyphenyl)-2-nitrobenzyl-trichloroacetate (35) at 365 nm (Scheme 3). The rate of photoconversion was monitored by HPLC, TLC and UV. Depending on the concentration of solution (0.002-2% in acetonitrile) and the length of light path used (1-10 mm) the rate of photoconversion varied between 20% and 90% for a 5 min irradiation. The products of photolysis, 2-nitrosobenzophenone (47) and 3′-methoxy-2-nitrosobenzophenone (48), were isolated by HPLC and showed by mass spectroscopy to be the same as those isolated previously during irradiations at 254 and 350 nm in the photoreactor described above. Secondary photoproducts were not observed under the conditions of relatively weak irradiation used in the photoreactor (4 W lamp), but were observed when the 100 W high pressure Hg arc lamp was used for extended time.

Workup

  1. customfor a 5 min
  2. customirradiation

Sources & evidence

ORD record
ord-02cb040a8fd2480d9cf07dd2380f522d
Source dataset
uspto-grants-2007_11
Patent number
US07301049B2

Reaction notes

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