Ethyl Acetate → 2-(4-Methoxymethylbenzoylamino)-2-(ethoxy)-acetonitrile
Reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:10][CH2:11][C:12]#[N:13])=[O:9])=[CH:6][CH:5]=1.BrBr.[C:18](OCC)(=[O:20])[CH3:19]>BrBr>[CH3:1][O:2][CH2:3][C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:10][CH:11]([O:20][CH2:18][CH3:19])[C:12]#[N:13])=[O:9])=[CH:6][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
A solution of 2-(4-methoxymethylbenzoylamino)-acetonitrile (5.0 g) in dry ethyl acetate (40 ml) was treated with a couple of drops of bromine and stirred at 30° C. until initiation of the reaction occurred. The bromine was then added dropwise keeping the temperature at 25°-30° C. After completion of the addition the mixture was filtered through celite, and the filtrate treated with ethanol (5 ml), with stirring, followed by triethylamine (5.0 g), at room temperature. After completion of the addition the mixture was stirred for 5 minutes, filtered through celite, and washed with water, dried over magnesium sulphate and evaporated at less than 30° C., giving a brown oil, (5.0 g). This was purified by preparative HPLC to yield the product as white needles (1.6 g), mpt 99°-100° C.
Workup
- customat 25°-30° C
- additionAfter completion of the addition the mixture
- filtrationwas filtered through celite
- additionthe filtrate treated with ethanol (5 ml)
- stirringwith stirring
- customfollowed by triethylamine (5.0 g), at room temperature
- additionAfter completion of the addition the mixture
- stirringwas stirred for 5 minutes
- filtrationfiltered through celite
- washwashed with water
- dry with materialdried over magnesium sulphate
- customevaporated at less than 30° C.
- customgiving a brown oil, (5.0 g)
- customThis was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-64f939b8a6c54a0ca7a8d4fdb5ff7c88
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04728665
Reaction notes
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