Potassium Bicarbonate → HCID 19974152, compound

HRID 1451450Notes

Reaction equation

HRID 1451450 reaction equation
[CH3:1][N:2]([C:4]1[S:5][CH:6]=[C:7]([C:9](=[O:12])[CH2:10]Br)[N:8]=1)[CH3:3].C(=O)([O-])O.[K+].Cl.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([NH2:32])[CH3:31])=[CH:25][CH:24]=1)([O:21][CH3:22])=[O:20]>CC(C)=O>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([NH:32][CH2:10][CH:9]([OH:12])[C:7]2[N:8]=[C:4]([N:2]([CH3:3])[CH3:1])[S:5][CH:6]=2)[CH3:31])=[CH:25][CH:24]=1)([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 19974146HCID 19974146, compoundHCID 199743502639411-66-6

Product 1

HCID 19974152HCID 19974152, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 g of 2-(N,N-dimethylamino)-4-bromoacetyl-thiazole in 250 ml of acetone are heated to reflux with 10 g of potassium hydrogen carbonate and 9.5 g of 2-(4-carbomethoxyphenyl)-1-methylethylamine-hydrochloride for 3 hours. After the reaction mixture has been cooled the inorganic products are removed by filtration, and the filtrate is concentrated in a rotary evaporator. The resulting oil residue is taken up in 150 ml of absolute methanol and, at 0°-5° C., 1.75 g of sodium borohydride are added in small portions. The mixture is then stirred at 0°-5° C. for one hour and at room temperature for 24 hours. Then ice-water are added to the reaction mixture, and it is acidified with concentrated hydrochloric acid, made alkaline with ammonia, while cooling in ice, and extracted with methylene chloride. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using ethyl acetate/methanol=8:2 as eluant.

Workup

  1. temperatureAfter the reaction mixture has been cooled the inorganic products
  2. customare removed by filtration
  3. concentrationthe filtrate is concentrated in a rotary evaporator
  4. customis taken up in 150 ml of absolute methanol and, at 0°-5° C.
  5. addition1.75 g of sodium borohydride are added in small portions
  6. additionThen ice-water are added to the reaction mixture, and it
  7. temperaturewhile cooling in ice
  8. extractionextracted with methylene chloride
  9. dry with materialThe extract is dried over sodium sulphate
  10. concentrationconcentrated
  11. custompurified on a silica gel column

Sources & evidence

ORD record
ord-895008d67ec44700b0e7475f2a481688
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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