Formaldehyde → HCID 18998482, compound

HRID 1742664Notes

Reaction equation

HRID 1742664 reaction equation
[Br:1][C:2]1[CH:31]=[C:30](N)[C:5]2[O:6][CH2:7][C:8]3[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=3[CH:10]([C:11]([NH:13][C:14]3[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=3[CH:23]([CH3:25])[CH3:24])=[O:12])[C:4]=2[CH:3]=1.[C:33]([BH3-])#[N:34].[Na+].[CH3:37]C1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.Cl.C(O)C.C=O>CO>[Br:1][C:2]1[CH:31]=[C:30]([N:34]([CH3:33])[CH3:37])[C:5]2[O:6][CH2:7][C:8]3[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=3[CH:10]([C:11]([NH:13][C:14]3[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=3[CH:23]([CH3:25])[CH3:24])=[O:12])[C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 18998475HCID 18998475, compound2×HCID 21887872Ethanol hydrochloride2×

Product 1

HCID 18998482HCID 18998482, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 2.12 g of 2-bromo-6,11-dihydro-N-(2,6-diisopropylphenyl)-4-aminodibenz[b,e]oxepin-11-carboxamide (Compound 54) obtained in Example 88 was dissolved in 80 ml of methanol. 1.35 g of sodium cyanoborohydride and a small amount of Bromocresol Green were added to the solution, and 5.8M hydrochloric acid-ethanol solution were added to the solution under ice cooling to render the solution yellow. While 1.74 g of 37% formalin was added dropwise to the mixture at room temperature, 5.8M hydrochloric acid-ethanol solution was added to keep the reaction solution yellow. After the reaction was completed, the reaction solution was concentrated under reduced pressure and ethyl acetate and water were added to the residue. The mixture was made alkaline with 10N sodium. hydroxide. The organic layer was washed with water and saturated sodium chloride aqueous solution successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane: ethyl acetate=5:1) to obtain 1.85 g of 2-bromo-6,11-dihydro-N-(2,6-diisopropylphenyl)-4-dimethylaminodibenz[b,e]oxepin-11-carboxamide.

Workup

  1. additionwere added to the solution under ice cooling
  2. concentrationthe reaction solution was concentrated under reduced pressure and ethyl acetate and water
  3. additionwere added to the residue
  4. washThe organic layer was washed with water and saturated sodium chloride aqueous solution successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane: ethyl acetate=5:1)

Sources & evidence

ORD record
ord-c846bb647f8344a2b9a5fc81a7b6d711
Source dataset
uspto-grants-1994_08
Patent number
US05340807

Reaction notes

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