Formaldehyde → HCID 22903495, compound

HRID 1440270Notes

Reaction equation

HRID 1440270 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:28])[C:13]3[S:17][C:16]([NH:18][C:19](=[O:27])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])=[CH:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([NH:29][CH3:30])[C:6]=2[CH:31]=1.C=O.[C:34]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:28])[C:13]3[S:17][C:16]([NH:18][C:19](=[O:27])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])=[CH:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([N:29]([CH3:34])[CH3:30])[C:6]=2[CH:31]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 22903503HCID 22903503, compound

Product 1

HCID 22903495HCID 22903495, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 7-chloro-5-methylamino-1-[5-(2-methylbenzoylamino)thenoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.5 g) in methanol (10 ml) are added 37% formaldehyde (0.8 ml) and sodium cyanoborohydride (0.1 g), and further thereto is added dropwise acetic acid (0.6 ml) at a temperature below 10° C. The mixture is stirred at room temperature for one hour, and poured into ice-water. The mixture is made basic with potassium carbonate, and extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-5-dimethylamino-1-[5-(2-methylbenzoylamino)thenoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.41 g) as colorless amorphous.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-58d58114096a4e91b7047a41368b12cf
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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