3,5-Dinitrobenzoyl chloride → HCID 53698818, compound

HRID 397244Notes

Reaction equation

HRID 397244 reaction equation
[SH:1][C:2]([CH3:9])([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][OH:5].[N+:10]([C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16](Cl)=[O:17])([O-:12])=[O:11].C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[SH:1][C:2]([CH3:9])([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][O:5][C:16](=[O:17])[C:15]1[CH:14]=[C:13]([N+:10]([O-:12])=[O:11])[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=1

Participants

5

Reactant 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 101300393-methyl-3-sulfanylhexan-1-ol

Product 1

HCID 53698818HCID 53698818, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.0 g (34 mmol) of (rac)-3-mercapto-3-methyl-hexan-1-ol in 20 ml of CCl4 was added in portions 8.6 g (37 mmol) of 3,5-dinitrobenzoyl chloride. The mixture was stirred for 72 h, then 10 ml of a saturated NaHCO3 solution was added, the organic layer was separated, washed with 15 ml of brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash-chromatography (silicagel, hexane/EtOAc 4:1) and gave 9.8 g (84%) of (rac)-3,5-dinitro-benzoic acid 3-mercapto-3-methyl-hexyl ester.

Workup

  1. customthe organic layer was separated
  2. washwashed with 15 ml of brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash-chromatography (silicagel, hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-52616f86bb344bd385a1109e156a15a8
Source dataset
uspto-grants-2003_08
Patent number
US06610346B1

Reaction notes

Loading…