Formaldehyde → HCID 75202150, compound

HRID 1480650Notes

Reaction equation

HRID 1480650 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[C:8]([OH:21])=[C:7]([CH2:22][NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:28]=O>C1COCC1>[C:24]([N:23]1[CH2:22][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=3)[C:8]=2[O:21][CH2:28]1)([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 71816504HCID 71816504, compound

Product 1

HCID 75202150HCID 75202150, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(tert-Butyl)-2-((tert-butylamino)methyl)-6-(6-(trifluoromethyl)pyridin-3-yl)phenol (2.00 g, 5.26 mmol) was added to a 37% aqueous solution of formaldehyde (0.47 mL, 5.78 mmol) in THF (6 mL) and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the solid was recrystallized by heating 1.1 g of product in methanol (10 mL) then cooling to room temperature to yield a first crop of 3,6-di-tert-butyl-8-(6-(trifluoromethyl)pyridin-3-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (588 mg, 29%) as a white crystalline solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solid was recrystallized
  3. temperatureby heating 1.1 g of product in methanol (10 mL)
  4. temperaturethen cooling to room temperature

Sources & evidence

ORD record
ord-c5d0d8b4983b4974b32cb24a5e39ed7c
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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