Triethylamine → S-(2-pyridinyl) 4-cyanobenzenecarbothioate

HRID 2250546Notes

Reaction equation

HRID 2250546 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[SH:7].C(N(CC)CC)C.[C:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)#[N:16]>O1CCCC1>[C:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21](=[O:22])[S:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 12548807S-(2-pyridinyl) 4-cyanobenzenecarbothioateYield 885.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-pyridinethiol (17 g) in tetrahydrofuran (200 mL) was added triethylamine (15.5 g) in an ice-water bath under N2. To this was added a solution of 4-cyanobenzoyl chloride (25.3 g) in tetrahydrofuran (80 mL) below 10° C. over 30 minutes. After 15 minutes, the bath was removed and the mixture was stirred overnight at ambient temperature. The mixture was concentrated in vacuo. The residue was partitioned between chloroform and water. The organic layer was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue (38 g) was triturated with isopropyl ether to give S-(2-pyridinyl) 4-cyanobenzenecarbothioate (325 g) as a pale brown solid.

Workup

  1. customthe bath was removed
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was partitioned between chloroform and water
  4. washThe organic layer was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue (38 g) was triturated with isopropyl ether

Sources & evidence

ORD record
ord-9c689e9ab7bb45cda69bf5d815f6159a
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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