N-dimethylaminomethylene-4-methyl-benzamide → 3-(4-p-Tolyl-[1,3,5]triazin-2-yl)benzoic acid

HRID 628821Notes

Reaction equation

CN([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)C.C([O:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[NH:29])[NH2:28])[CH:22]=1)(C)(C)C>C(O)(=O)C>[C:10]1([CH3:13])[CH:11]=[CH:12][C:7]([C:6]2[N:5]=[CH:4][N:28]=[C:27]([C:23]3[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=3)[C:20]([OH:19])=[O:30])[N:29]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 115 °C

Procedure

Part D. A mixture of N-dimethylaminomethylene-4-methyl-benzamide (221.9 mg, 1.15 mmol) and 3-carbamimidoyl-benzoic acid tert-butyl ester (196.0 mg, 0.89 mmol) in anhydrous acetic acid (8 mL) is heated to 115° C. at 150 W, 250 psi in a microwave reactor for 30 min. until complete consumption of the starting material is determined by TLC. A white solid is precipitated by addition of 1 N HCl, and collected by filtration, followed by washing with water and hexanes. The obtained solid is further purified by flash column chromatography, eluting with methanol/methylene chloride (1:20) to afford the title product (23.1 mg, 5.3% yield), m.p. 298-300° C. 1H NMR (300 MHz, DMSO-d6): δ 9.40 (1H, s), 8.63 (2H, d, J=8.3 Hz), 8.48 (2H, d, J=8.0 Hz), 8.13 (2H, d, J=8.0 Hz), 7.41 (2H, m), 2.41 (3H, s). MS (ES+): m/e 292.30.

Workup

customA white solid is precipitated by addition of 1 N HCl
filtrationcollected by filtration
washby washing with water and hexanes
customThe obtained solid is further purified by flash column chromatography
washeluting with methanol/methylene chloride (1:20)

Sources & evidence

ORD record: ord-cb43800a18a94c5fa4f07f1fcd9ab08b
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315467B2

Reaction notes

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