Ethanol → HCID 56637441, compound

HRID 2352652Notes

Reaction equation

HRID 2352652 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[S:11])=[CH:5][CH:4]=1)#[N:2].[C:12]1([S:18]([NH2:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].[CH2:24](O)C.CI>CC(C)=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[N:21][S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])[S:11][CH3:24])=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 702EthanolHCID 6328Methyl iodideHCID 7370BenzenesulfonamideHCID 14798Sodium HydroxideHCID 17626Benzonitrile, 4-isothiocyanato-

Product 1

HCID 56637441HCID 56637441, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 5 g (0.031 mol) of 4-cyanophenyl isothiocyanate, of 6.3 g (0.04 mol) of benzenesulfonamide in 50 cm3 of acetone and of 1.6 g (0.04 mol) of sodium hydroxide in 3 cm3 of water is maintained for two hours at room temperature. The precipitate obtained is filtered, washed with acetone and ethyl ether (2×20 cm3). The final solid (9 g; yield 94%) is then placed in 50 cm3 of 95% ethanol containing 2.75 cm3 (0.044 mol) of methyl iodide. After 24 hours at room temperature the solution is concentrated to dryness and the residue is washed with ethyl ether (3×20 cm3) and dried in vacuo. 8.5 g (yield 80%) of N-(4-cyanophenyl)-N'-phenylsulfonyl-S-methylisothiourea (melting point 150° C.) is obtained: ##STR23##

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered
  3. washwashed with acetone and ethyl ether (2×20 cm3)
  4. concentrationAfter 24 hours at room temperature the solution is concentrated to dryness
  5. washthe residue is washed with ethyl ether (3×20 cm3)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-67ffcb328f6248c295c4867e760d20f4
Source dataset
uspto-grants-1989_10
Patent number
US04877895

Reaction notes

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