Acetone → HCID 20096454, compound

HRID 1769967Notes

Reaction equation

HRID 1769967 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[N:9][S:10][C:6]=2[C:5]=1[C:13](OC)=[O:14].CC(C)=O.Cl>O.O1CCCC1>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[N:9][S:10][C:6]=2[C:5]=1[CH2:13][OH:14]

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

To a suspension of 4.5 g of sodium borohydride in 30 ml of water and 70 ml of tetrahydrofuran there are added dropwise with stirring and heating to 40°-50° C. in the course of haft an hour a solution of 1.9 g of 6-chloro-7-carbomethoxybenzo-1,2,3-thiadiazole in 30 ml of tetrahydrofuran (dissolved under hot conditions). Heating of the mixture is continued until the reaction is complete, and the mixture is then cooled to -20° to -30° C. using a CO2 cooling bath and treated dropwise with 15 ml of acetone, during which process gas is evolved vigorously. The reaction mixture is subsequently brought to pH 3 using 15% hydrochloric acid, with further vigorous cooling at -20° to -10° C. (evolution of gas), and stirring is continued overnight. Most of the tetrahydrofuran is then evaporated on a rotary evaporator, and the residue is extracted using ethyl acetate. The extracts are washed with water, dried over sodium sulfate and evaporated. The residue gives the title compound of m.p. 138°-140° C.

Workup

  1. additionthere are added dropwise
  2. temperatureHeating of the mixture
  3. temperaturethe mixture is then cooled to -20° to -30° C.
  4. temperaturewith further vigorous cooling at -20° to -10° C. (evolution of gas)
  5. stirringstirring
  6. customMost of the tetrahydrofuran is then evaporated on a rotary evaporator
  7. extractionthe residue is extracted
  8. washThe extracts are washed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-d16ac65348164e4994093d64e3224ae4
Source dataset
uspto-grants-1995_01
Patent number
US05384321

Reaction notes

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