1,2,3-Benzothiadiazol-7-ylmethanol → Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

HRID 1769960Notes

Reaction equation

HRID 1769960 reaction equation
[OH:1][CH2:2][C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[S:10]1[C:11]2[C:3]([CH:2]=[O:1])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=[N:9]1

Participants

4

Reactant 1

HCID 200964331,2,3-Benzothiadiazol-7-ylmethanol

Product 1

HCID 14835681Benzo[d][1,2,3]thiadiazole-7-carbaldehydeYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

To a solution of 16.6 g of 7-hydroxymethylbenzo-1,2,3-thiadiazole in 100 ml of chloroform there are introduced with stirring at room temperature 35 g of manganese dioxide, during which process the internal temperature rises briefly to 31 ° C. When the temperature has dropped again to 25° C., the mixture is heated and refluxed overnight. Another 5 g of manganese dioxide are subsequently added, and heating of the mixture is continued until the reaction is complete. The hot mixture is filtered over Hyflo and the filtrate is then evaporated. The residue is digested in a little hexane and then filtered, which gives 15 g (91.4%) of the title compound of m.p. 134°-136° C.

Workup

  1. customrises briefly to 31 ° C
  2. additionWhen the temperature has dropped again to 25° C.
  3. temperaturethe mixture is heated
  4. temperaturerefluxed overnight
  5. temperatureheating of the mixture
  6. filtrationThe hot mixture is filtered over Hyflo
  7. customthe filtrate is then evaporated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1710cd5ab47f42e5bab9e473985dbd92
Source dataset
uspto-grants-1995_01
Patent number
US05384321

Reaction notes

Loading…