Benzyl mercaptan → HCID 23226996, compound

HRID 1956171Notes

Reaction equation

HRID 1956171 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[C:11]1[C:12]([S:17]([CH3:20])(=O)=O)=[N:13][CH:14]=[N:15][CH:16]=1.C(S)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[H-].[Na+].[H][H]>O1CCCC1.CCCCCC.[OH-].[Na+]>[CH2:20]([S:17][C:12]1[C:11]([CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10][C:2]2([CH3:21])[CH3:1])=[CH:16][N:15]=[CH:14][N:13]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 23226984HCID 23226984, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23226996HCID 23226996, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 6.7 g of impure 5-(2,2-dimethyl-1-indanyl)-4-methanesulfonylpyrimidine (approximately 6.1 g (0.20 mol) in 50 mL of dry tetrahydrofuran was prepared and to this was added with stirring 2.5 mL (2.6 g, 0.21 mol) of benzyl mercaptan and then, in several small portions, 0.84 g of 60 percent sodium hydride in mineral oil (0.21 mol). Hydrogen was evolved and the mixture became cloudy. After about 4 hr the mixture was diluted with 200 mL of hexane and 150 mL of 2N aqueous sodium hydroxide. The phases were separated and the organic phase was washed with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure to obtain 7.6 g of crude product. This was dissolved in hexane and flash chromatographed on silica gel eluting first with hexane (10×200 mL) and then with a 25:75 by volume mixture of dichloromethane and hexane (14×200 mL) and then with dichloromethane 12×200 mL). There was desired product in fractions 12-36 and these fractions were combined and the resulting mixture was concentrated by evaporation under reduced pressure at 50° C. to obtain 6.3 g of the title compound as a white solid melting at 76°-79° C.

Workup

  1. additionto this was added
  2. customThe phases were separated
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customto obtain 7.6 g of crude product
  7. customflash chromatographed on silica gel eluting first with hexane (10×200 mL)
  8. additionwith a 25:75 by volume mixture of dichloromethane and hexane (14×200 mL)
  9. concentrationthe resulting mixture was concentrated by evaporation under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-6d436ba0a2974d30bf4f43cc7f2f4c4a
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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