Benzyl mercaptan → HCID 12415655, compound

HRID 236785Notes

Reaction equation

HRID 236785 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[H-].[Na+]>CN(C)C=O.O>[NH2:16][C:15]1[C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[S:8][C:1]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 133912-ChlorobenzonitrileHCID 24758Sodium hydrideHCID 10942334Sodium Methoxide

Product 1

HCID 12415655HCID 12415655, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

from 10.5 g (84 mmol) of benzylmercaptan and the equimolar quantity of sodium methoxide the corresponding salt is prepared. A solution of sodium benzylthiolate is stirred for 1 hour at ambient temperature in 150 milliliters of absolute dimethyl formamide after the addition of 10.5 g (76 mmol) of 2-chloro-benzonitrile and 8.0 g of a disbursion of NaH at 50% (0.167 mol). The mixture is then poured into water and the product extracted with CH2Cl2. By evaporating the organic phase dried over Na2SO4 and re-crystallising the residue in cyclohexane, 16.0 g (93% of theory) of 3-amino-2-phenyl--benzo(b)thiophene are obtained, yellow plates, mp 110°-112° C.

Workup

  1. extractionthe product extracted with CH2Cl2
  2. customBy evaporating the organic phase
  3. dry with materialdried over Na2SO4
  4. customre-crystallising the residue in cyclohexane

Sources & evidence

ORD record
ord-09d55bf9dcbc43708735e26bd259a6e2
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Reaction notes

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