Dimethylamine → HCID 11735930, compound

HRID 2081351Notes

Reaction equation

HRID 2081351 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[CH3:12][NH:13][CH3:14].[CH2:15]=O>CO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:7]([OH:11])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 121243-Hydroxyacetanilide

Product 1

HCID 11735930HCID 11735930, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-acetamidophenol (15.25 g, 101 mmol) in 40% dimethylamine (13.8 ml, 122 mmol) and 13 ml of methanol, was added 37% formalin (8.3 ml, 101 mmol). The reaction mixture was placed in an ice bath just after the precipitate formed (about 15--30 minutes). The white precipitate was filtered after 10-30 minutes, washed with cold water, and air-dried to give 13.7 g (65%) of 5-acetamido-2-[(dimethylamino)methyl]phenol, m.p. 133-135° C.

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. customjust after the precipitate formed (about 15--30 minutes)
  3. filtrationThe white precipitate was filtered after 10-30 minutes
  4. washwashed with cold water
  5. customair-dried

Sources & evidence

ORD record
ord-66fd8de08dcb4889873c17835d525b18
Source dataset
uspto-grants-1993_02
Patent number
US05183941

Reaction notes

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