2,3-Dichloroaniline → 3-(2,3-Dichloroanilino)-4-(2-hydroxyanilino)-cyclobut-3-ene-1,2-dione

HRID 1743137Notes

Reaction equation

C(O[C:4]1[C:5](=[O:17])[C:6](=[O:16])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])C.[Cl:18][C:19]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21]>C1(C)C=CC=CC=1.CS(C)=O>[Cl:18][C:19]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][C:4]1[C:5](=[O:17])[C:6](=[O:16])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-ethoxy-4-(2-hydroxyanilino)-cyclobut-3-ene-1,2-dione (100 mg, 0.43 mmol) in toluene (2 mL) and DMSO (1 drop) was added 2,3-dichloroaniline (0.07 mL, 0.43 mmol) and reaction was stirred at 110° C. overnight. The resulting solid was collected by filtration, washed with ethyl acetate to remove toluene and dried in vacuo. LC-MS (m/z) 349 (M+).

Workup

filtrationThe resulting solid was collected by filtration
washwashed with ethyl acetate
customto remove toluene
customdried in vacuo

Sources & evidence

ORD record: ord-e9617ac0878e431ca77d660b77514c97
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008962B2

Reaction notes

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