Ethanol → Ethyl 2-amino-alpha-methylbenzothiazole-6-acetate

HRID 34532Notes

Reaction equation

HRID 34532 reaction equation
[CH2:1]([OH:3])[CH3:2].[OH:4]S(O)(=O)=O.[NH2:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([CH:19]([CH3:22])[C:20]#N)[CH:16]=[CH:15][C:13]=2[N:14]=1>O>[NH2:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([CH:19]([CH3:22])[C:20]([O:3][CH2:1][CH3:2])=[O:4])[CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 134779396-Benzothiazoleacetonitrile, 2-amino-alpha-methyl-

Product 1

HCID 13477940Ethyl 2-amino-alpha-methylbenzothiazole-6-acetateYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 10 ml of 95% ethanol, 10 g of conc. H2SO4, and 0.5 g of the compound of Step A above was heated at reflux for 20 hours and the mixture was then cooled, diluted with water and the ethanol was evaporated off. The resulting solution was neutralized with sodium bicarbonate to obtain a solid which was collected and crystallized from methanol/water to obtain 0.38 g (61%) of ethyl 2-amino-α-methylbenzothiazole-6-acetate as off-white needles melting at 146° C.

Workup

  1. temperatureat reflux for 20 hours
  2. temperaturethe mixture was then cooled
  3. customthe ethanol was evaporated off
  4. customto obtain a solid which
  5. customwas collected
  6. customcrystallized from methanol/water

Sources & evidence

ORD record
ord-e5b17d068b1f4c0c82a77a8d2cbab1e8
Source dataset
uspto-grants-1988_08
Patent number
US04762840

Reaction notes

Loading…