Dimethylformamide → HCID 58468226, compound

HRID 1430586Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].CN(C=O)C.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7]([Cl:24])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (4.00 g, 19.7 mmol) in CH2Cl2 (90 mL) cooled at 0° C. was added DMF (76 μL, 0.98 mmol) and oxalyl chloride (2.15 mL, 24.6 mmol). The reaction was allowed to warm to ambient temperature and stirred for 3.5 h. The solution was concentrated in vacuo to provide 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl chloride as a yellow-orange oil which gave a mass ion (ES+) of 218.2. 1H NMR δ (ppm) (CDCl3): 7.89 (2H, s), 7.76 (1H, d, J=8.2 Hz), 7.59-7.60 (1H, m), 7.48-7.50 (1 H, m), 2.48 (3H, s).

Workup

temperatureto warm to ambient temperature
concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-9fb03901bc05470db2e9aee63a564792
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940898B2

Reaction notes

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