Formaldehyde → HCID 66590530, compound

HRID 2363499Notes

Reaction equation

HRID 2363499 reaction equation
[CH2:1]=O.CO.[F:5][C:6]([F:21])([F:20])[C:7]1[CH:8]=[C:9]([CH:17]=[CH:18][CH:19]=1)[CH2:10][NH:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14].[C:22](=[O:25])([O-])[O-].[K+].[K+]>>[CH3:1][O:25][CH2:22][N:11]([CH2:10][C:9]1[CH:17]=[CH:18][CH:19]=[C:7]([C:6]([F:20])([F:5])[F:21])[CH:8]=1)[CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 66591171HCID 66591171, compound

Product 1

HCID 66590530HCID 66590530, compound

Conditions

Temperature
0 °C

Procedure

Formaldehyde (4.08 g, 50.2 mmol) and methanol (2.032 mL, 50.2 mmol) were combined, and the mixture was cooled to 0° C. (ice bath). N-(3-(trifluoromethyl)benzyl)-1-(trimethylsilyl)methanamine (10.94 g, 41.9 mmol) was added dropwise via addition funnel over 30 minutes. Potassium carbonate (4.63 g, 33.5 mmol) was added, and the reaction stirred at 0° C. for 2 additional hours. The reaction product was decanted from the potassium carbonate, treated with more potassium carbonate, and decanted again. The potassium carbonate solids were washed several times with ether, and these washes were added to the product solution. The solvent was removed in vacuo to give 1-methoxy-N-(3-(trifluoromethyl)benzyl)-N-((trimethylsilyl)methyl)methanamine which was used directly in the next step.

Workup

  1. customThe reaction product was decanted from the potassium carbonate
  2. additiontreated with more potassium carbonate
  3. customdecanted again
  4. washThe potassium carbonate solids were washed several times with ether
  5. additionthese washes were added to the product solution
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4f56c97ea89f4b268a626f5e2a8f927f
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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