Dimethylformamide → HCID 68686395, compound

HRID 1159010Notes

Reaction equation

HRID 1159010 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>C(Cl)Cl>[CH2:26]([N:28]([CH2:29][CH3:30])[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[O:3][C:2]([F:1])([F:14])[F:13])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 65578Oxalyl chlorideHCID 27772232-(Trifluoromethoxy)benzoic acid

Product 1

HCID 68686395HCID 68686395, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirring solution of 2-trifluoromethoxybenzoic acid (3.6 g, 17.5 mmol, Avocado) in dry CH2Cl2 (150 mL) with DMF (0.5 mL) was added a 2M solution of oxalyl chloride in CH2Cl2 (17.5 mL) dropwise over 30 min. The reaction was stirred for 4 h and then conc. in vacuo to a white solid. The solid was dissolved in CH2Cl2 (150 mL) and reacted with diethylamine (3.2 g, 43.8 mmol, Aldrich) the reaction was stirred for 16 h and then conc. in vacuo to a yellow solid. The solid was purified by radial chromatography (SiO2, 1:5, EtOAc:hexanes) to yield 4.3 grams (94%) of the product as a colorless oil. MS (ESI) 262 (M+H).

Workup

  1. stirringwas stirred for 16 h
  2. customThe solid was purified by radial chromatography (SiO2, 1:5, EtOAc:hexanes)

Sources & evidence

ORD record
ord-316c8062ef604dc899ca31346e8af8ae
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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