Potassium Carbonate → (2,3-Dihydro-1,4-benzoxathiin-2-yl)acetonitrile

HRID 1065245Notes

Reaction equation

HRID 1065245 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([CH2:20]Br)[CH2:17][C:18]#[N:19]>CC(C)=O>[O:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH2:20][CH:16]1[CH2:17][C:18]#[N:19]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 118311393,4-Dibromobutanenitrile2×

Product 1

HCID 20540157(2,3-Dihydro-1,4-benzoxathiin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To the refluxing solution of 75 g of 2-hydroxythiophenol [J. Pharm. Sci. 61, 2 (1972)] in 660 ml of acetone is added 42 g of potassium carbonate, followed by the dropwise addition of the solution of 33.5 g of 3,4-dibromobutyronitrile in 50 ml of acetone while stirring. After 30 minutes refluxing, a second, third, and fourth addition of 42 g potassium carbonate and 33.5 g of 3,4-dibromobutyronitrile is made. The whole mixture is refluxed for 20 hours, cooled and filtered. The filtrate is evaporated and the residue distilled in a bulb to bulb apparatus at 185° and 0.5 mmHg, to yield the 2-(1,4-benzoxathian-2-yl)-acetonitrile.

Workup

  1. temperatureAfter 30 minutes refluxing
  2. temperatureThe whole mixture is refluxed for 20 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. distillationthe residue distilled in a bulb to bulb apparatus at 185°

Sources & evidence

ORD record
ord-0d8011befb4e43cfb0443e48d396f840
Source dataset
uspto-grants-1982_05
Patent number
US04329348

Reaction notes

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