Sodium Hydroxide → 80019-85-8

HRID 848231Notes

Reaction equation

HRID 848231 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-9d1908fc8be946c881186b1b7d7aad53
Source dataset
uspto-grants-1981_10
Patent number
US04294986

Reaction notes

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