Water → HCID 19082070, compound

HRID 963307Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[Cl:10].C(N(CC)CC)C.Cl[C:19]([O:21][CH3:22])=[O:20].O>C(C(C)=O)C>[Cl:10][C:3]1[C:4]([CH2:8][CH3:9])=[N:5][CH:6]=[CH:7][C:2]=1[NH:1][C:19](=[O:20])[O:21][CH3:22]

Participants

Conditions

Temperature: -10 °C

Procedure

5.7 g (36.4 mmol) of 4-amino-3-chloro-2-ethylpyridine was dissolved in 50 ml of methyl ethyl ketone. Then, 5.5 g (54.6 mmol) of triethylamine was added thereto, and the mixture was stirred at -10° C. Then, 8.6 g (91.0 mmol) of methyl chloroformate was gradually added thereto so that the temperature would not exceed -5° C. After completion of the dropwise addition, the mixture was stirred for one hour at a temperature of from -10° to -5° C. and for further one hour at room temperature. Then, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was recrystallized from isopropyl ether to obtain 5.0 g of the desired product as colorless prism crystals (melting point: 78° to 79° C.).

Workup

customexceed -5° C
additionAfter completion of the dropwise addition
stirringthe mixture was stirred for one hour at a temperature of from -10° to -5° C. and for further one hour at room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThen, ethyl acetate was distilled off under reduced pressure
customThe obtained residue was recrystallized from isopropyl ether

Sources & evidence

ORD record: ord-b08e3a64636a480a8819a68626e6a0d4
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763463

Reaction notes

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