Chloroacetonitrile → 4-[(Cyanomethyl)sulfanyl]benzoic acid

HRID 1361024Notes

Reaction equation

HRID 1361024 reaction equation
[OH-].[Na+].[SH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]#[N:22]>O>[C:21]([CH2:20][S:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)#[N:22]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 957384-Mercaptobenzoic acid

Product 1

HCID 201149864-[(Cyanomethyl)sulfanyl]benzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of sodium hydroxide (10.4 g, 0.26 mol) in degassed water (600 mL) was added 4-mercaptobenzoic acid (20.0 g, 0.13 mol). This solution was stirred for 30 minutes. To a solution of potassium carbonate (9.0 g, 65 mmol) in degassed water (400 mL) was added chloroacetonitrile (9.8 g, (0.13 mol) portion-wise. These two solutions were mixed and stirred for 48 hours at RT under N2. The mixture was filtered and washed with heptane. The aqueous phase was acidified with 3N hydrochloric acid and the product was filtered off, washed with water and dried, affording 4-cyanomethylsulfanylbenzoic acid (27.2 g, 88%). This compound was used without further purification in the following step.

Workup

  1. additionThese two solutions were mixed
  2. stirringstirred for 48 hours at RT under N2
  3. filtrationThe mixture was filtered
  4. washwashed with heptane
  5. filtrationthe product was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-8ee104ad16c04450b412973933bfd468
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

Loading…