Formaldehyde → HCID 24857671, compound

HRID 556148Notes

Reaction equation

HRID 556148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]([NH:19][CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:21]=O.[OH-].[K+]>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]([N:19]([CH3:21])[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 24857670HCID 24857670, compound

Product 1

HCID 24857671HCID 24857671, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The respective methylamine 7 (e.g., 28.4 mg, 0.0927 mmol) was dissolved in 96% formic acid (0.5 mL) and 37% aqueous formaldehyde (0.5 mL) and heated at 100° C. for two hours. After cooling, the solution was basicified (aq KOH) and extracted with MTBE. The organic phase was dried with sodium sulfate, filtered, and evaporated to give the dimethylamine (e.g., 27.1 mg, 93%) as a clear oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with MTBE
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-565109e2f4764e60895a33a59e5593d5
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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