Formaldehyde → HCID 9921267, compound

HRID 11400Notes

Reaction equation

HRID 11400 reaction equation
C=O.[Cl:3][C:4]1[CH:15]=[C:14]2[C:7]([NH:8][C:9]([CH2:16][CH3:17])=[C:10]2[CH2:11][CH2:12]N)=[CH:6][CH:5]=1.[C:18]([BH3-])#[N:19].[Na+].[C:22]([O-])([O-])=O.[K+].[K+]>CO.CC(O)=O>[Cl:3][C:4]1[CH:15]=[C:14]2[C:7]([NH:8][C:9]([CH2:16][CH3:17])=[C:10]2[CH2:11][CH2:12][N:19]([CH3:18])[CH3:22])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 21974280HCID 21974280, compound

Product 1

HCID 9921267HCID 9921267, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

40% HCHO (0.95 mL) in MeOH (16 mL) was added dropwise to a stirred cooled (0° C.) solution of (5) (3.16 mmol), AcOH (0.47 mL) and sodium cyanoborohydride (0.35 g). The resulting mixture was allowed to stir at 25° C. for 2.5 h. A saturated aqueous solution of K2CO3 (5 mL) was added, MeOH was removed in vacuo and the aqueous phase was extracted with EtOAc. After drying over Na2SO4, the solvent was evaporated under reduced pressure to give a crude residue which was purified by filtration on silica gel.

Workup

  1. customMeOH was removed in vacuo
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialAfter drying over Na2SO4
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-07f7b555c74944509c2041118cd716bb
Source dataset
uspto-grants-2006_08
Patent number
US07098233B2

Reaction notes

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