Benzyl Chloride → HCID 12837900, compound

HRID 1065306Notes

Reaction equation

HRID 1065306 reaction equation
[C:1]([NH:4][C:5](=[O:11])[CH2:6][S:7][C:8](=O)[CH3:9])(=[O:3])[CH3:2].[H-].[Na+].[H][H].C(Cl)[C:17]1[CH:22]=[CH:21]C=[CH:19][CH:18]=1>CN(C)C=O>[C:1]([NH:4][C:5](=[O:11])[CH2:6][S:7][CH2:8][C:9]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 12837856N-acetyl-2-(acetylthio)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 12837900HCID 12837900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.75 g. (0.01 mole) of N-acetyl-2-(acetylthio) acetamide in 20 ml. of dimethylformamide was added 0.5 g. of 50% sodium hydride. After evolution of hydrogen stopped, there was added 1.5 ml. of benzyl chloride and the reaction mixture was heated on a steam bath for 4 hours. The product was chromatographed by thin layer chromatography eluting with 40% ethylacetate/hexane, then 15 g. of silica gel was added and the product was stripped in vacuo. The prepack was chromatographed on 200 g. of silica gel, eluting with 15% ethylacetate/hexane. A yield of 0.65 g. of product was recrystallized from isopropanol, m.p. 86°-87° C.

Workup

  1. additionthere was added 1.5 ml
  2. customThe product was chromatographed by thin layer chromatography
  3. washeluting with 40% ethylacetate/hexane
  4. additionof silica gel was added
  5. customThe prepack was chromatographed on 200 g
  6. washof silica gel, eluting with 15% ethylacetate/hexane
  7. customof product was recrystallized from isopropanol, m.p. 86°-87° C.

Sources & evidence

ORD record
ord-ed84f8680b72452897ce1123d9ecf8ed
Source dataset
uspto-grants-1982_05
Patent number
US04329363

Reaction notes

Loading…