Chloroform → HCID 20084584, compound

HRID 1609283Notes

Reaction equation

HRID 1609283 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:32])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](=[O:31])[CH3:30])=[CH:20][CH:19]=1)#[N:2].[BH4-].[Na+].C(Cl)(Cl)Cl>O1CCCC1.CO>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:32])[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([OH:31])[CH3:30])=[CH:22][CH:23]=1)#[N:2]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 20084436HCID 20084436, compound

Product 1

HCID 20084584HCID 20084584, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran was suspended 3.33 g of N-[2-(2-cyanophenylthio)phenyl]-4-(5-oxohexyloxy)benz-amide (prepared in accordance with Reference Example 6, Step 2) followed by addition of a solution of 0.31 g of sodium borohydride in methanol, and the mixture was stirred for 1 hour. To the reaction mixture was added chloroform and the mixture was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate-n-hexane to give 3.15 g of the title compound as white crystals.

Workup

  1. washthe mixture was washed with saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-e5124195e9134832b1331333fe0b7e28
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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