Dimethylformamide dimethyl acetal → HCID 178499302、化合物

HRID 1181364ノート

反応式

HRID 1181364 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 178499302HCID 178499302、化合物収率 98.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-40570bafd0fa49c79789ea12d3f0b8ad
出典データセット
uspto-grants-2007_10
特許番号
US07285557B2

反応ノート

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