Formaldehyde → HCID 15581948, compound

HRID 1580451Notes

Reaction equation

HRID 1580451 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% formalin solution. The reaction is kept at 25°C. for 12 hours, then refluxed for 4 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 4 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-314d895c73294fcc85ef68f01d8ce671
Source dataset
uspto-grants-1976_01
Patent number
US03932641

Reaction notes

Loading…