Methanol → Methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate

HRID 2414260Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:6]([O:8][CH3:9])=[O:7].[O-:14][C:15]#[N:16].[K+].CO.CN(C)[CH:22]=[O:23]>C(OCC)(=O)C.O>[Cl:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:2][NH:16][C:15]([O:23][CH3:22])=[O:14]

Participants

Conditions

Temperature: 90 °C

Procedure

16.0 g of the obtained methyl 3-bromomethyl-4-chlorobenzoate, 15.0 g of potassium cyanate and 35 ml of methanol were added to 200 ml of N,N-dimethylformamide, followed by stirring at 90° C. for 4 hours. After completion of the reaction, water was added to the reaction mixture, extraction with ethyl acetate was carried out, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropanol to obtain 25.2 g of methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate as white crystals.

Workup

dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe obtained crude crystals
washwere washed with isopropanol

Sources & evidence

ORD record: ord-d4526409a12a456bb193fe73c51b7090
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812229B1

Reaction notes

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