Dimethylformamide dimethyl acetal → HCID 178499302, compound

HRID 1181364Notes

Reaction equation

HRID 1181364 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16][CH3:17])=[O:15].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>C(O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]([C:14]([O:16][CH3:17])=[O:15])=[C:2](/[N:1]=[CH:20]/[N:21]([CH3:23])[CH3:22])[CH:6]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

Product 1

HCID 178499302HCID 178499302, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (37.3 mmol, 10.0 g) and N,N-dimethylformamide dimethyl acetal (74.7 mmol, 8.9 g) in ethanol (350 mL) was heated at reflux for 3 hours. The solvent was removed by rotary evaporation. To the residue 15 mL of toluene was added and the solvent was removed by rotary evaporation. This was repeated three times. To the resulting sticky residue, 20 mL hexanes was added followed by the gradual addition of ethyl acetate at 0° C. until it solidified. The resulting solid was collected by filtration giving the product (11.9 g, 98.9%). 1H NMR (CDCl3): δ 3.08 (6H, d, J=6.5 Hz), 3.81 (3H, s),6.98 (1 H. s), 7.35 (2H, d, J=8.6 Hz), 7.53 (2H, d, J=8.5 Hz), 7.69 (1H, s). LCMS m/z=323 (m+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed by rotary evaporation
  4. additionTo the residue 15 mL of toluene was added
  5. customthe solvent was removed by rotary evaporation
  6. additionTo the resulting sticky residue, 20 mL hexanes was added
  7. additionfollowed by the gradual addition of ethyl acetate at 0° C. until it
  8. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-40570bafd0fa49c79789ea12d3f0b8ad
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

Loading…