Diethyl (ethoxymethylene)malonate → HCID 178469650, compound
Reaction equation
[C:1]([S:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([F:11])[CH:5]=1)#[N:2].C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C1CCCCC1.C1(C)C=CC=CC=1>[C:1]([S:3][C:4]1[CH:10]=[C:9]2[C:7](=[C:6]([F:11])[CH:5]=1)[N:8]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]2[OH:14])#[N:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 48 g of 4-(cyanosulfanyl)-2-fluoroaniline and 57.7 g of diethyl ethoxymethylenemalonate is stirred at 130° C. After 1.5 h the mixture is diluted with 200 mL of a 1:1 mixture of cyclohexane and toluene. The mixture is cooled to 0° C. and the precipitate collected by filtration. It is washed with two 75 mL portions of a 1:1 mixture of cyclohexane and toluene, dried in a stream of air, and then it dissolved in 400 mL of diphenyl ether. The mixture is refluxed for 1 h and then cooled to 25° C. It is diluted with 1 L of 1:1 toluene/cyclohexane and the precipitate collected by filtration. The solid is dried in a stream of air to give 20 g of the title compound.
Workup
- temperatureThe mixture is cooled to 0° C.
- filtrationthe precipitate collected by filtration
- washIt is washed with two 75 mL portions of a 1:1 mixture of cyclohexane and toluene
- customdried in a stream of air
- dissolutionit dissolved in 400 mL of diphenyl ether
- temperatureThe mixture is refluxed for 1 h
- temperaturecooled to 25° C
- additionIt is diluted with 1 L of 1:1 toluene/cyclohexane
- filtrationthe precipitate collected by filtration
- customThe solid is dried in a stream of air
Sources & evidence
- ORD record
- ord-6fd1bc196b2840c584dfa2e59ce55978
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093732
Reaction notes
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