1,1'-(Diazomethylene)bis(benzene) → HCID 86748958, compound

HRID 2399285Notes

Reaction equation

[NH2:1][C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:11]([C:14]([CH3:18])([CH3:17])[CH2:15][CH3:16])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].[C:27]1([C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N+]=[N-])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[CH:33]([OH:4])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH2:1][C:2]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:18])[CH2:15][CH3:16])=[CH:10][C:6]=1[C:7]([O-:9])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

2-(amino-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzoic acid (150 mg, 0.0004 mol) was dissolved in toluene and diphenyldiazomethane was added. The mixture was heated to 50° C., under argon, and stirred for 4 h. The solvents were evaporated and the residue was flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CDCl3) δ7.98 (d, 1H), 7.45 (dd, 1H), 7.24 (s, 10H), 6.83-6.98 (m, 4H), 6.65 (d, 1H), 3.93 (s, 2H), 1.64 (s, 2H), 1.29 (s, 6H), 0.69 (t, 3H).

Workup

customThe solvents were evaporated
customchromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-e3d6a9dcb8c2489dac61d70b8729c559
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05447957

Reaction notes

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