Dimethylformamide → HCID 18626234, compound

HRID 1859661Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH2:19][CH3:20])[C:13]([OH:15])=O)([O-])=O.CN(C=O)C.[F:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[F:34])[NH2:30]>>[NH2:7][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH2:19][CH3:20])[C:13]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([F:34])=[C:27]([F:26])[CH:28]=1)=[O:15]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 65578Oxalyl chloride

HCID 774693,4-Difluoroaniline

HCID 81670864-Ethyl-3-nitrobenzoic acid

Product 1

HCID 18626234HCID 18626234, compoundYield 89.8%

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (2.0 mL, 22.93 mmol), 3-nitro-4-ethylbenzoic acid from Example 17, Step A (3.85 g, 19.74 mmol), DMF (1.0 mL, 12.92 mmol), and 3,4-difluoroaniline (4.0 mL, 40.34 mmol) to afford the product (4.9 g); m.p. 108-110° C. after trituration in hexane.

Workup

customPrepared

Sources & evidence

ORD record: ord-f82cd3ab788742ecb87524026e445473
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528528B2

Reaction notes

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