Dimethylamine, hydrochloride → 2-Chloro-4-dimethylamino-5-fluoro-benzoic acid methyl ester

HRID 1041884Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7](F)=[CH:6][C:5]=1[Cl:12].Cl.[CH3:15][NH:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:16]([CH3:17])[CH3:15])=[CH:6][C:5]=1[Cl:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 23.1 g (112 mmol) 22a and 231 ml dimethylsulphoxid were added 10.0 g (123 mmol) dimethylamine hydrochloride and 32.4 g (234 mmol) potassium carbonate. The reaction mixture was stirred for 24 h at 60° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 22b was obtained in 89.5% yield (23.1 g 100 mmol).

Workup

customwas reduced with high vacuum rotation evaporator at 65° C
additionThe residue was diluted with dichloromethane
washwashed twice with water
extractionThe combined water phases were extracted with dichloromethane
washThe combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution
dry with materialdried with sodium sulphate
concentrationconcentrated
customThe oily crude was purified by column chromatography

Sources & evidence

ORD record: ord-a5da3aca25e04b2495e77b5ffce1bd20
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557776B2

Reaction notes

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