Dimethyl Sulfoxide → HCID 59255198, compound

HRID 78235Notes

Reaction equation

HRID 78235 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.[BH4-].[Na+].O>C(O)(=O)C>[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 4311764Sodium borohydrideHCID 592553371-Benzylsulfanyl-4-((E)-2-nitro-vinyl)-benzene

Product 1

HCID 59255198HCID 59255198, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-benzylsulfanyl-4-((E)-2-nitro-vinyl)-benzene (950 mg, 3.5 mmol) described in Manufacturing Example 205-1-3 in acetic acid (0.6 mL) and dimethyl sulfoxide (10 mL) was added sodium borohydride (212 mg, 5.6 mmol) while the internal temperature was held at 30° C. or lower, which was stirred for 30 minutes at room temperature. The mixture was cooled with ice water, water was added, which was stirred for another 30 minutes. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (936 mg). The title compound was used in the following reaction without any further purification.

Workup

  1. customwas held at 30° C.
  2. additionwas added
  3. stirringwhich was stirred for another 30 minutes
  4. customThis mixture was partitioned into ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-dadb4748695d472cb63b1522be131323
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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