(2-Thienylmethyl)amine → HCID 10198071, compound

HRID 2082364Notes

Reaction equation

HRID 2082364 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[C:8](N1C=CN=C1)([N:10]1[CH:14]=[CH:13]N=C1)=[S:9].COC(OC)CN>C1(C)C=CC=CC=1>[S:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH2:2][N:1]1[CH:13]=[CH:14][NH:10][C:8]1=[S:9]

Participants

5

Reactant 3

HCID 34005(2-Thienylmethyl)amineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10198071HCID 10198071, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under a blanket of nitrogen, 11.3 g (0.1 mol) 2-aminomethylthiophene is added to 19.6 g (0.11 mol) 1,1'-thiocarbonyldiimidazole in 200 ml anhydrous toluene at 0° C. the reaction is held at 0° C. for 4 hours. Then 10.5 g (0.1 mol) aminoacetaldehyde dimethyl acetal is added and the reaction is warmed at 80° C. for 2 hours. The toluene is removed and the residue dissolved in 100 ml ethanol, 15 ml water and 15 ml concentrated HCl. The mixture is refluxed 5 hours, cooled and poured into 1 L ice. After recrystallization (1/1 EtOH/H2O) the desired product is obtained as white shiny crystals, mp 128-130° C.

Workup

  1. customThe toluene is removed
  2. dissolutionthe residue dissolved in 100 ml ethanol
  3. temperatureThe mixture is refluxed 5 hours
  4. temperaturecooled
  5. additionpoured into 1 L ice
  6. customAfter recrystallization (1/1 EtOH/H2O) the desired product
  7. customis obtained as white shiny crystals, mp 128-130° C.

Sources & evidence

ORD record
ord-494e4d610d0945f780f9c347cfb253f9
Source dataset
uspto-grants-1993_02
Patent number
US05189052

Reaction notes

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