Lawesson's reagent → [2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 4-thiocarbamoyl-phenyl ester

HRID 44162

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=O)[NH2:27])=[CH:22][CH:21]=1)=[O:18].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1C=CC=CC=1>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][C:17](=[O:18])[CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[CH:21][CH:22]=1)(=[S:38])[NH2:27]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Carbamoylphenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (5, 480 mg, 1.14 mmol) and Lawesson reagent (460 mg, 1.14 mmol) were dissolved in 20 ml of anhydrous benzene. The reaction was warmed to 50° C. and stirred for 6 h. The solvent was removed under reduced pressure; the crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.5/0.5) to furnish the pure compound 6 (446 mg, 91% yield).

Workup

customThe solvent was removed under reduced pressure
customthe crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.5/0.5)

Sources & evidence

ORD record: ord-dbcaec4b035a431aa1b6d6e73b38b402
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541398B2

Linked notes

Loading…