Diphenyl Ether → 8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 718033Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].C1(OC2C=CC=CC=2)C=CC=CC=1>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:13])[NH:1][C:2]=2[CH:7]=1

Participants

Reactant 2

HCID 7583Diphenyl Ether

HCID 610730N-(2-Amino-4-chlorophenyl)anthranilic acid

Product 1

HCID 36531168-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-oneYield 76.1%

Conditions

Temperature: 175 °C

Procedure

The 2-(2-amino-4-chlorophenylamino)benzoic acid (2.00 g, 7.63 mmol) was mixed with diphenyl ether (5 mL). The reaction mixture was stirred at 175° C. for 2 hours. The mixture was cooled down to room temperature and put directly to the column eluting with 10% to 50% ethyl acetate in hexanes to afford the title compound 9 (1.42 g, 76%) as a purple solid.

Workup

temperatureThe mixture was cooled down to room temperature
washeluting with 10% to 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-b165c80520d54ac3a933ada0c4ac8d96
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193749B2

Reaction notes

Loading…