Sodium Hydroxide → 80019-85-8

HRID 1577954Notes

Reaction equation

HRID 1577954 reaction equation
[BH4-].[Na+].[S].[CH2:4]([S:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[Cl:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>O1CCCC1.C(O)C.C(OCC)(=O)C>[ClH:22].[CH2:4]([S:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=1[Cl:22])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 5362487SulfurHCID 12942110HCID 12942110, compound

Product 1

HCID 1294211280019-85-8

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21584252Ethanol ethylacetateSolvent

Procedure

Dry tetrahydrofuran (THF; 20 ml) is added to a mixture of sodium borohydride (1.89 g; 0.05 mol) and sulfur (4.8 g; 0.15 mol). Vigorous gas evolution commences and the reaction mixture is cooled in a cold water bath. After the gas evolution ceases, a solution of 2-chloro-4-nitrophenyl phenethyl sulfide (14.65 g; 0.05 mol) in dry THF (50 ml) is added to the above mixture. The reaction mixture is stirred for 15 hours at room temperature and then at 80° C. for 2 hours. It is then cooled down, 20% sodium hydroxide (30 ml) added, and the mixture extracted with ether. The extract is washed with water, saturated brine and dried over magnesium sulfate. Ethanolic hydrogen chloride solution is added dropwise to the ethereal solution to precipitate the title product. The product is isolated by filtration, washed with ether and dried to afford 10.4 g (69%), m.p. 213°-214° C. (d). A sample is prepared for analysis by recrystallization from ethanol-ethyl acetate m.p. 213°-214° C. (d).

Workup

  1. temperatureVigorous gas evolution commences and the reaction mixture is cooled in a cold water bath
  2. waitat 80° C. for 2 hours
  3. temperatureIt is then cooled down
  4. extractionthe mixture extracted with ether
  5. washThe extract is washed with water, saturated brine
  6. dry with materialdried over magnesium sulfate
  7. additionEthanolic hydrogen chloride solution is added dropwise to the ethereal solution
  8. customto precipitate the title product
  9. customThe product is isolated by filtration
  10. washwashed with ether
  11. customdried
  12. customto afford 10.4 g (69%), m.p. 213°-214° C. (d)

Sources & evidence

ORD record
ord-bea3114c39c340378670307314a5eca4
Source dataset
uspto-grants-1981_09
Patent number
US04289903

Reaction notes

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