Sodium borohydride → HCID 20278969, compound

HRID 1248226Notes

Reaction equation

HRID 1248226 reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:14][CH2:15][CH2:16][OH:17])[CH3:13])=[O:4].[BH4-].[Na+]>CN(C)C=O>[OH:17][CH2:16][CH2:15][N:14]1[CH:12]([CH3:13])[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20278973HCID 20278973, compound

Product 1

HCID 20278969HCID 20278969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 135 parts of N,N-dimethylformamide are added first 16.2 parts of 2,2,2-trichloro-N-[2-[1-[(2-hydroxyethyl)imino]ethyl]phenyl]acetamide and then portionwise 5.7 parts of sodium borohydride while stirring: exothermic reaction. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto water and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 8.5 parts of 3,4-dihydro-3-(2-hydroxyethyl)-4-methyl-2(1H)-quinazolinone as a solid residue.

Workup

  1. customexothermic reaction
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated

Sources & evidence

ORD record
ord-63b3ec2347f34bdd860525e5c3599bf7
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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