Dimethylformamide dimethyl acetal → HCID 178499302, 화합물

HRID 1181364노트

반응식

HRID 1181364 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 178499302HCID 178499302, 화합물수율 98.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-40570bafd0fa49c79789ea12d3f0b8ad
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285557B2

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