Water → HCID 5067622, compound

HRID 1414169Notes

Reaction equation

HRID 1414169 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.O.[C:11]1([S:17]([CH2:20][C:21]#[N:22])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1CCCCC1>C1C=CC=CC=1.C(O)(=O)C>[C:2]1([CH3:1])[CH:9]=[CH:8][C:5]([CH:6]=[C:20]([C:21]#[N:22])[S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:18])=[O:19])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 8082PiperidineHCID 82077Phenylsulphonylacetonitrile

Product 1

HCID 5067622HCID 5067622, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Conditions

Temperature
10 °C

Procedure

120 g (1 mole) of p-methylbenzaldehyde were heated to the boil on a water separator and under reflux with 181 g (1 mole) of phenylsulfonyl-acetonitrile in 500 ml benzene with addition of 6 ml of piperidine and 3 ml of glacial acetic acid. After 5 hours, 17 ml water had separated. Upon cooling to 10° C, the 1-p-tolyl-2-cyano-2-phenylsulfonyl-ethlene crystallized; after suction filtration, washing with 150 ml of cold benzene and drying, 206 g (73% of the theory) were obtained; melting point: 145°-147° C. ##STR14##

Workup

  1. custom17 ml water had separated
  2. customthe 1-p-tolyl-2-cyano-2-phenylsulfonyl-ethlene crystallized
  3. filtrationafter suction filtration
  4. washwashing with 150 ml of cold benzene
  5. customdrying
  6. custom206 g (73% of the theory) were obtained

Sources & evidence

ORD record
ord-c74855fa121342b7bcbd38b2cb8c4f3d
Source dataset
uspto-grants-1977_01
Patent number
US04001221

Reaction notes

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