Hydrochloric Acid → 2-Cyano-6-hydroxybenzothiazole

HRID 1761662Notes

Reaction equation

HRID 1761662 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C-:12]#[N:13].[K+].C1OCCOCCOCCOCCOCCOC1.Cl>CS(C)=O>[C:12]([C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1)#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 147498432-Chlorobenzo[d]thiazol-6-ol2×

Product 1

HCID 98819122-Cyano-6-hydroxybenzothiazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

4 g. of the mixture of 2-chloro-6-hyroxybenzothiazole and 2-iodo-6-hydroxybenzothiazole obtained in Example 2 are added to a suspension of 3 g. potassium cyanide and 100 mg. 18-crown-6 in 150 ml. dimethyl sulphoxide heated to 120° C. and stirred at a bath temperature of 120° C. After a reaction time of 3 hours, the reaction mixture is poured in 1 liter of ice water and the solution obtained is acidified with dilute hydrochloric acid. Subsequently, it is extracted twice with 500 ml. amounts of diethyl ether and the extracts are washed with water, dried over anhydrous sodium sulphate, mixed with charcoal, filtered and the filtrate evaporated in a vacuum. 2.5 g. Crude 2-cyano-6-hydroxybenzothiazole are obtained.

Workup

  1. additionare added to a suspension of 3 g
  2. customthe solution obtained
  3. extractionSubsequently, it is extracted twice with 500 ml
  4. washamounts of diethyl ether and the extracts are washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. additionmixed with charcoal
  7. filtrationfiltered
  8. customthe filtrate evaporated in a vacuum

Sources & evidence

ORD record
ord-204b057f413642c3bcfade2af9efddc5
Source dataset
uspto-grants-1989_05
Patent number
US04826989

Reaction notes

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