Dimethylamine → HCID 11735930, compound

HRID 1111508Notes

Reaction equation

HRID 1111508 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 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 30.5 g (202 mmol) of 3-acetamidophenol in 27.5 g (244 mmol) of 40% dimethylamine and 25 ml of methanol, was added 16.4 g (202 mmol) of 37% formalin. The reaction mixture was placed in an ice bath just after the precipitate formed (ABOUT 15 minutes). The white precipitate was filtered after 15-30 minutes, washed with cold water, and air-dried to give 28.0 g (67% yield) of 5-acetamido-2-[(N,N-dimethylamino)-methyl]phenol.

Workup

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

Sources & evidence

ORD record
ord-7488ecefa4f547128f18bac65644d367
Source dataset
uspto-grants-1990_12
Patent number
US04980505

Reaction notes

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