Acetone → HCID 21925588, compound

HRID 1243567Notes

Reaction equation

HRID 1243567 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].CC(C)=O.Br[CH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]>O>[Cl:20][C:18]1[CH:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]([CH:19]=1)[CH2:13][S:1][CH2:2][C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 124231272-(Bromomethyl)-4-chloro-1-nitrobenzene

Product 1

HCID 21925588HCID 21925588, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mercapto-acetic acid (1.39 ml, 20 mmol) was dissolved in a 3.3 molar aqueous solution of sodium hydroxide (12 ml, 40 mmol) and cooled in an ice bath, before an acetone (50 ml) solution of 2-Bromomethyl-4-chloro-1-nitro-benzene (T. J. McCord et al, J. Het. Chem. 1972, 119–122)(5 g, 20 mmol) was added slowly. The resulting solution was stirred for 20 hours at room temperature before being diluted with water (50 ml) and extracted with dichloromethane (25 ml). The aqueous phase was made acidic with acetic acid and extracted with dichloromethane (2×25 ml). The combined organics were washed with brine, dried (MgSO4), filtered and evaporated to give the title product as an off-white foam (3.65 g).

Workup

  1. additionwas added slowly
  2. extractionextracted with dichloromethane (25 ml)
  3. extractionextracted with dichloromethane (2×25 ml)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-427e80176c484a05ba45443fcf8a8357
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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