Dimethylformamide → 2-(p-Tolyl)benzamide

HRID 247821Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C[N:18](C)C=O.C(Cl)(=O)C(Cl)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH2:18])=[O:16])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4'-Methyl[1,1'-biphenyl]-2-carboxylic acid, prepared as in European Patent Application 87-109919.8 Example 85-a, page 147, line 32 (20.0 g, 94.2 mmol) in dichloromethane (200 mL) at 0° C. was added dimethylformamide (0.5 mL) followed by oxalyl chloride (375 mL of 2.0 M solution in dichloromethane, 750 mmol). The rate of addition was adjusted to maintain the internal temperature below 10° C. When the addition was complete, the mixture was allowed to warm to 25° C. and was stirred at that temperature for two hours, after which it was concentrated in vacuo. The semisolid residue was added portionwise to concentrated ammonium hydroxide solution (250 mL) at 0° C., stirred for 15 minutes, and diluted with water (200 mL). The resulting white precipitate was collected, washed with water, and dried in vacuo over phosphorus pentoxide to give the title compound (18.7 g, 90%).

Workup

additionThe rate of addition
temperatureto maintain the internal temperature below 10° C
additionWhen the addition
concentrationafter which it was concentrated in vacuo
additionThe semisolid residue was added portionwise to concentrated ammonium hydroxide solution (250 mL) at 0° C.
stirringstirred for 15 minutes
additiondiluted with water (200 mL)
customThe resulting white precipitate was collected
washwashed with water
dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record: ord-550beafd3c3b4c8a894a513539329550
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05208234

Reaction notes

Loading…