Formaldehyde → HCID 15581948, compound

HRID 1579201Notes

Reaction equation

HRID 1579201 reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([NH2:6])=[S:5].[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:22]=O>CO>[CH3:1][CH:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([NH:6][CH2:14][N:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[S:5]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7515N-MethylanilineHCID 15581943α-(1-Methylethyl)-2-pyridineethanethioamide

Product 1

HCID 15581948HCID 15581948, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.94 g. (0.01 mole) of 3-methyl-2-(2-pyridyl)thiobutanamide in 40 ml. of methanol is treated with 1.6 g. (0.015 mole) of N-methylaniline and 1.22 ml. of 37 percent formalin solution. The reaction is kept at 25°C. for 12 hours, then refluxed for four hours. The solvents are evaporated in vacuo and the residue is triturated with ethyl acetate and cooled, then filtered. The filtrate is evaporated in vacuo and the resulting oil is triturated with cold ether to give 3-methyl-N-(N-methyl-N-phenylaminomethyl)-2-(2-pyridyl)thiobutanamide, which after recrystallization from ether melts at 95°-97°C.

Workup

  1. temperaturerefluxed for four hours
  2. customThe solvents are evaporated in vacuo
  3. customthe residue is triturated with ethyl acetate
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe filtrate is evaporated in vacuo
  7. customthe resulting oil is triturated with cold ether

Sources & evidence

ORD record
ord-e9ec5e08a1824aeb825fce3ba8549337
Source dataset
uspto-grants-1976_01
Patent number
US03931162

Reaction notes

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