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

HRID 1155961Notes

Reaction equation

HRID 1155961 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-abc1965639fa46989fda20d5b52bbd2c
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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