2-Thiophenecarboxaldehyde → HCID 12337032, compound

HRID 1775417Notes

Reaction equation

HRID 1775417 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][NH2:12]>C1(C)C=CC=CC=1>[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][N:12]=[CH:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 12337032HCID 12337032, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of thiophene-2-carboxaldehyde (7.5 mL, 82.3 mmol, Alfa Aesar), aminoacetaldehyde dimethyl acetal (8.82 mL, 82.3 mmol, Alfa Aesar) in 100 mL toluene was heated to 115° C. using a Dean-Stark trap to remove water. After 3 hours, the reaction was cooled to room temperature. The reaction was placed on a rotary evaporator to evaporate the toluene, which yielded a brown liquid (about 17.3 g), which was used without further manipulation in the next step. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.42 (6H, s), 3.73 (1H, d, J=5.3 Hz), 4.65 (1H, t, J=5.3 Hz), 7.07-7.41 (3H, m).

Workup

  1. customto remove water
  2. customThe reaction was placed on a rotary evaporator
  3. customto evaporate the toluene, which

Sources & evidence

ORD record
ord-19edc7740fe048f6b4bf1ea80305bcfe
Source dataset
uspto-grants-2016_02
Patent number
US09260450B2

Reaction notes

Loading…