Acetone → HCID 20096454, compound

HRID 1464421Notes

Reaction equation

HRID 1464421 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[N:7][S:8][C:4]=2[C:3]=1[C:11](OC)=[O:12].[BH4-].[Na+].CC(C)=O.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[N:7][S:8][C:4]=2[C:3]=1[CH2:11][OH:12]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20096435HCID 20096435, compound

Product 1

HCID 20096454HCID 20096454, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.9 g of 6-chloro-7-carbomethoxybenzo-1,2,3-thiadiazole in 30 ml of tetrahydrofuran (dissolved hot) is added dropwise to a suspension of 4.5 g of sodium borohydride in 30 ml of water and 70 ml of tetrahydrofuran in the course of half an hour, while stirring and heating at 40°-50° C. Heating is continued until the reaction is complete, the mixture is cooled to -20° to -30° C. with a CO2 cooling bath and 15 ml of acetone are added dropwise, vigorous evolution of gas being observed. The reaction mixture is then acidified to pH 3 with 15% hydrochloric acid at -20° C. to -10° C., with further vigorous cooling (evolution of gas), and stirring is continued overnight. The majority of the tetrahydrofuran is then stripped off on a rotary evaporator and the residue is extracted with ethyl acetate. The extracts are washed with water, dried over sodium sulfate and evaporated. The residue gives the title compound of melting point 138°-140° C.

Workup

  1. temperatureheating at 40°-50° C
  2. temperatureHeating
  3. temperaturethe mixture is cooled to -20° to -30° C. with a CO2 cooling bath
  4. temperaturewith further vigorous cooling (evolution of gas)
  5. stirringstirring
  6. customThe majority of the tetrahydrofuran is then stripped off on a rotary evaporator
  7. extractionthe residue is extracted with ethyl acetate
  8. washThe extracts are washed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-9774a835d2c9462c921ed49e948e7ec7
Source dataset
uspto-grants-1994_04
Patent number
US05304652

Reaction notes

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