Thionyl Chloride → HCID 68295574, compound

HRID 572521Notes

Reaction equation

[CH3:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)=[O:5].S(Cl)(Cl)=O.[CH3:24][NH:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].CCN(C(C)C)C(C)C>C(OCC)(=O)C.CN(C)C=O>[CH3:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([N:25]([CH3:24])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[O:10])=[O:5]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(2,4-dimethylbenzoyl)benzoic acid (50 g, 197 mmol) and thionyl chloride (215 mL, 2949 mmol) was heated at 70° C. for 1.5 hours. The mixture was concentrated, dissolved in tetrahydrofuran (THF) (200 mL) and N,N-dimethylformamide (DMF) (40 mL) and treated with methyl N-methylglycinate (27.4 g, 197 mmol). The mixture was cooled to 0° C. and treated with Hunig's base (103 mL, 590 mmol). The mixture was heated to 70° C. for 1 hour, cooled to ambient temperature and then diluted with ethyl acetate. The organic phase was washed with 1N HCl, water, then brine, dried over sodium sulfate, filtered and concentrated to a brown thick oil (60 g, 90%) which was used without further purification. LC/MS (m/z) ES+=340 (M+1).

Workup

concentrationThe mixture was concentrated
dissolutiondissolved in tetrahydrofuran (THF) (200 mL)
temperatureThe mixture was cooled to 0° C.
temperatureThe mixture was heated to 70° C. for 1 hour
temperaturecooled to ambient temperature
washThe organic phase was washed with 1N HCl, water
dry with materialbrine, dried over sodium sulfate
filtrationfiltered
concentrationconcentrated to a brown thick oil (60 g, 90%) which
customwas used without further purification

Sources & evidence

ORD record: ord-d06420e1425943feac1b0e45aec6e4bf
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029391B2

Reaction notes

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