Dimethyl Sulfoxide → 2-Chloro-6-sulfanylbenzonitrile

HRID 869374Notes

Reaction equation

HRID 869374 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](Cl)[C:3]=1[C:4]#[N:5].C[S:12](C)=O>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([SH:12])[C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 3031Dichlobenil

Product 1

HCID 212247652-Chloro-6-sulfanylbenzonitrile

Procedure

The solution of 2,6-dichloro-benzonitrile (20 mmol) in DMSO (dimethyl sulfoxide, 30 mL) was heated to 70° C., followed by addition of Na2S.9H2O portionwise under stirring. The mixture was stirred for 1 hour. TLC monitored the reaction. After the reaction completed, the mixture was cooled and extracted between water and ethyl acetate. The aqueous layer was acidified by hydrochloric acid to pH=3˜4 under stirring. The formed solids were collected by filtration and dried to give 2.3 g of 2-chloro-6-mercapto-benzonitrile (2A). MS (ESI): M++1=170.6.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. customthe reaction
  3. temperaturethe mixture was cooled
  4. extractionextracted between water and ethyl acetate
  5. stirringunder stirring
  6. filtrationThe formed solids were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-1fa06ab57c4b4f6690ceda09a4b7aa5c
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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