Diphenylamine → HCID 90460544, compound

HRID 1487572Notes

Reaction equation

Br[C:2]1[C:19]2[C:20]3[C:5]([C:6]4[C:23]5[C:10](=[C:11]([C:25]([OH:27])=[O:26])[CH:12]=[C:13]([Cl:24])[C:14]=5[C:15]=3[C:16]([Cl:22])=[CH:17][C:18]=2Br)[C:9]([C:28](O)=[O:29])=[CH:8][C:7]=4[Cl:31])=[C:4]([Cl:32])[CH:3]=1.[C:33]1([NH:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[Cl:24][C:13]1[CH:12]=[C:11]2[C:25](=[O:26])[O:27][C:28](=[O:29])[C:9]3[CH:8]=[C:7]([Cl:31])[C:6]4[C:5]5[C:4]([Cl:32])=[CH:3][C:2]6[C:45]7[C:40]([N:39]([C:33]8[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=8)[C:18]8[C:19]=6[C:20]=5[C:15]([C:14]=1[C:23]=4[C:10]2=3)=[C:16]([Cl:22])[CH:17]=8)=[CH:41][CH:42]=[CH:43][CH:44]=7

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 9,10-dibromo-1,6,7,12-tetrachloroperylene-3,4-dicarboxylic acid anhidride (1.24 g, 2.0 mmol), diphenylamine (0.40 g, 2.40 mmol), Pd(AcO)2 (10 mmol %), sodium-tert-butoxide (0.48 g, 5.0 mmol), tricyclohexylphosphine (20 mol %) in 70 ml toluene was stirred at 100° C. under argon atmosphere for 24 h. The solvent was removed under reduced pressure. The solid was dissolved in dichloromethane and acetic acid and stirred overnight at 70° C. The solvent was removed under reduced pressure. The crude product was purified by column chromatography using dichloromethane as eluent on silica. Yield 0.50 g (40%).

Workup

customThe solvent was removed under reduced pressure
dissolutionThe solid was dissolved in dichloromethane
stirringacetic acid and stirred overnight at 70° C
customThe solvent was removed under reduced pressure
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-d0e1522edebc412b9ef4af0bb10ef3ee
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428518B2

Reaction notes

Loading…