Water → N-[(2,3-Dihydro-1H-inden-2-yl)carbamothioyl]benzamide

HRID 1287895Notes

Reaction equation

HRID 1287895 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1.O>CC(C)=O>[C:5]([NH:3][C:2]([NH:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)=[S:1])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 763102-Aminoindane

Product 1

HCID 21507070N-[(2,3-Dihydro-1H-inden-2-yl)carbamothioyl]benzamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

To a stirred solution of ammonium thiocyanate (0.837 g.) in acetone (5 ml.) was added benzoyl chloride (1.406 g.) in acetone (10 ml.). The mixture was refluxed for 5 minutes then 2-aminoindane (1.332 g.) in acetone (10 ml.) was added quickly. Refluxing was continued for 10 minutes and the mixture poured into water (75 ml.) to give an oil which solidified on standing. Recrystallisation from ethanol/water afforded the title compound as pale yellow needles (2.151 g.), m.p. 130°-5° C.

Workup

  1. temperatureThe mixture was refluxed for 5 minutes
  2. temperatureRefluxing
  3. customto give an oil which
  4. customRecrystallisation from ethanol/water

Sources & evidence

ORD record
ord-2818b60ef8164b189d5ffba3fcc91c5a
Source dataset
uspto-grants-1976_10
Patent number
US03985898

Reaction notes

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