Formaldehyde → HCID 86718784, compound

HRID 929604Notes

Reaction equation

HRID 929604 reaction equation
[CH2:1]=O.[C:3]([NH2:7])([CH3:6])([CH3:5])[CH3:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20](O)=CC=[C:17]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[N:16]=2)=[CH:11][CH:10]=1.[CH2:29]([OH:32])[CH2:30][CH3:31]>>[C:3]([N:7]1[CH2:31][C:30]2[CH:20]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=3)[N:16]=[C:17]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:29]=2[O:32][CH2:1]1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 10311-Propanol2×HCID 6385Tert-ButylamineHCID 86718785HCID 86718785, compound

Product 1

HCID 86718784HCID 86718784, compoundYield 25%

Conditions

Temperature
80 °C

Procedure

A mixture of paraformaldehyde (235 mg, 7.83 mmol) and tert-butylamine (0.83 mL, 7.83 mmol) in 1-propanol (5 mL) was heated at 80° C. under nitrogen for 2 hours. A solution of 2,6-bis(4-chlorophenyl)pyridin-3-ol (420 mg, 1.33 mmol) in 1-propanol (5 mL) was then added and the reaction mixture refluxed for 6 days. The reaction mixture was cooled to room temperature, stood for 24 hours and filtered to afford 3-(tert-butyl)-6,8-bis(4-chlorophenyl)-3,4-dihydro-2H-pyrido[4,3-e][1,3]oxazine (135.8 mg, 25% yield) as an orange crystalline solid.

Workup

  1. temperaturethe reaction mixture refluxed for 6 days
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered

Sources & evidence

ORD record
ord-6ef7cec99c414a579d34ac216f2928ec
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

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