Water → 5-Cyano-2,3-dihydro-3,3-dimethyl-2-isothiocyanatobenzofuran

HRID 444087Notes

Reaction equation

HRID 444087 reaction equation
Cl[CH:2]1[C:6]([CH3:8])([CH3:7])[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.[S-:15][C:16]#[N:17].[K+].O>CN(C)C=O>[C:13]([C:10]1[CH:11]=[CH:12][C:4]2[O:3][CH:2]([N:17]=[C:16]=[S:15])[C:6]([CH3:8])([CH3:7])[C:5]=2[CH:9]=1)#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 516872Potassium thiocyanateHCID 205362092-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 205362295-Cyano-2,3-dihydro-3,3-dimethyl-2-isothiocyanatobenzofuranYield 21.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran (5 g) from Example 15 and potassium thiocyanate (4.6 g) were heated in dimethylformamide (30 ml) at 110° C. for 7 hours. The mixture, after cooling, was added to water and the product extracted into diethyl ether. The ether solution was washed with water (twice), dried over magnesium sulphate and run down under vacuum yielding 4 g of crude product. Purification by silica gel chromatography in toluene yielded 1.2 g of title product, mp 52° C.

Workup

  1. temperatureThe mixture, after cooling
  2. extractionthe product extracted into diethyl ether
  3. washThe ether solution was washed with water (twice),
  4. dry with materialdried over magnesium sulphate
  5. customyielding 4 g of crude product
  6. customPurification by silica gel chromatography in toluene

Sources & evidence

ORD record
ord-632947a72b384ee4833bda6bef6d884f
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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