Formaldehyde → HCID 22070441, compound

HRID 1879236Notes

Reaction equation

HRID 1879236 reaction equation
[CH2:1]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.C=O.[BH4-].[Na+].F[C:25](F)(F)C(O)=O.[OH-].[Na+].[Cl-].[Na+]>O.C1COCC1>[CH2:11]([N:10]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1)[CH3:25])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

9

Reactant 6

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10621178HCID 10621178, compound

Product 1

HCID 22070441HCID 22070441, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

10.0 g of N,N-Di(3-Anisyl)amine were dissolved 436 ml of anhydrous THF. 14.0 g of paraformaldehyde were added with stirring followed by 8.20 g of sodium borohydride. 190 ml of trifluoro acetic acid were added during 120 min and after completion of the addition the reaction mixture was stirred at room temperature over night. The reaction mixture was poured into 654 ml of an ice cubes containing 25.0%-weight solution of sodium hydroxide in water. After addition of 654 ml of a saturated aqueous solution of sodium chloride it was extracted three times with each 650 ml of dichloromethane and the combined organic extracts were dried with anhydrous sodium sulfate. After filtration the solvent was removed in vacuo and the crude product purified by fractionated distillation in vacuo. At a temperature of 125-135° C./0.04 mbar 8.60 g (80.4%) of DAMA are collected as yellow liquid.

Workup

  1. additionafter completion of the addition the reaction mixture
  2. stirringwas stirred at room temperature over night
  3. extractionwas extracted three times with each 650 ml of dichloromethane
  4. dry with materialthe combined organic extracts were dried with anhydrous sodium sulfate
  5. filtrationAfter filtration the solvent
  6. customwas removed in vacuo
  7. distillationthe crude product purified by fractionated distillation in vacuo
  8. customAt a temperature of 125-135° C./0.04 mbar 8.60 g (80.4%) of DAMA are collected as yellow liquid

Sources & evidence

ORD record
ord-a8596c46f6504f3684036eb0414badf9
Source dataset
uspto-grants-2012_11
Patent number
US08314162B2

Reaction notes

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