Formaldehyde → HCID 49761011, compound

HRID 907325Notes

Reaction equation

HRID 907325 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C=O.[Cl:21][CH2:22]Cl>[Cl-].[Cl-].[Zn+2]>[Cl:21][CH2:22][C:14]1[CH:15]=[CH:16][C:11]([CH:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])[CH2:6][CH2:7]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 18348438HCID 18348438, compound

Product 1

HCID 49761011HCID 49761011, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A suspension of the product of step i) (18 g), paraformaldehyde (14 g) and zinc dichloride (14 g) in dichloromethane (700 mL) was stirred at room temperature. Hydrogen chloride gas was bubbled through the reaction for 30 minutes. The reaction was stirred at room temperature under a blanket of nitrogen for a further 18 hours. Water (150 mL) was added and the phases separated. The organic phase was dried using magnesium sulfate and concentrated in vacuo to give a green oil which was purified (SiO2 eluting with 30% i-hexane in dichloromethane) to give the sub-title compound (12 g).

Workup

  1. customHydrogen chloride gas was bubbled through the reaction for 30 minutes
  2. stirringThe reaction was stirred at room temperature under a blanket of nitrogen for a further 18 hours
  3. additionWater (150 mL) was added
  4. customthe phases separated
  5. customThe organic phase was dried
  6. concentrationconcentrated in vacuo
  7. customto give a green oil which
  8. customwas purified (SiO2 eluting with 30% i-hexane in dichloromethane)

Sources & evidence

ORD record
ord-4211c398d5a84595bd5eea2f647d830a
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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