Sodium borohydride → HCID 20278969, compound

HRID 1156340Notes

Reaction equation

HRID 1156340 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-dimethylforamide 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-32088d4365eb4065808afe4bd7f3df83
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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