3-Hydroxybenzaldehyde → HCID 7986269, compound

HRID 1199697Notes

Reaction equation

HRID 1199697 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.C(OC(=O)C)(=O)C>C(O)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)/[CH:5]=[CH:10]/[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7918Acetic AnhydrideHCID 84462-Methylbenzothiazole

Product 1

HCID 7986269HCID 7986269, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 25 g of 3-hydroxybenzaldehyde, 36.6 g of 2-methylbenzothiazole, 38.8 ml of acetic anhydride and 7.7 ml of formic acid was heated at 120° C. for 25 hours. The low boiling materials were evaporated together with toluene under reduced pressure, and the residue was added to 150 ml of methanol and refluxed with addition of 3 g of potassium carbonate for 1 hour. After cooled to room temperature, the mixture was filtered and filtrate was concentrated. The crude product formed was washed with methanol and ethyl ether and dried under reduced pressure to obtain 20.6 g (yield 40%) of the title compound.

Workup

  1. customThe low boiling materials were evaporated together with toluene under reduced pressure
  2. additionthe residue was added to 150 ml of methanol
  3. temperaturerefluxed with addition of 3 g of potassium carbonate for 1 hour
  4. temperatureAfter cooled to room temperature
  5. filtrationthe mixture was filtered
  6. concentrationfiltrate was concentrated
  7. customThe crude product formed
  8. washwas washed with methanol and ethyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-23e9e6b152714fd79360bb2b1718ee16
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

Loading…