Dimethylformamide → HCID 86656259, compound

HRID 221382Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(Cl)(=O)C([Cl:31])=O.CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([Cl:31])=[O:24])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 3-(2′,4′-dichlorobiphenyl-4-ylsulfonamido)benzoic acid (1.50 g, 3.56 mmol) in DCM (35 mL) was stirred at 0° C. and oxalyl chloride (340 μL, 3.9 mmol) was added, followed by a catalytic amount of DMF (<50 μL). The mixture was allowed to warm to room temperature and stirred for two days, during which time the solid dissolved to form a light yellow clear solution. The mixture was evaporated under reduced pressure and the residue was azeotroped with toluene (3 mL), then hexane (10 mL) and the title compound obtained as a light brown, slightly gummy, solid (1.5 g) which was used without further purification.

Workup

temperatureto warm to room temperature
stirringstirred for two days, during which time the solid
dissolutiondissolved
customto form a light yellow clear solution
customThe mixture was evaporated under reduced pressure
customthe residue was azeotroped with toluene (3 mL)

Sources & evidence

ORD record: ord-5a21c4556dd8419cb5b4b454fde0a520
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207167B2

Reaction notes

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