Methylamine → 6-Methoxy-N,2-dimethyl-1-benzothiophene-3-carboxamide

HRID 1825058ノート

反応式

HRID 1825058 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](Cl)=[O:12])=[C:9]([CH3:14])[S:8][C:7]=2[CH:15]=1.[CH3:16][NH2:17]>C1COCC1>[CH3:16][NH:17][C:11]([C:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][C:7]=2[S:8][C:9]=1[CH3:14])=[O:12]

参加物

4

反応物 2

HCID 6329MethylamineHCID 22143646HCID 22143646、化合物

生成物 1

HCID 207678726-Methoxy-N,2-dimethyl-1-benzothiophene-3-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of this crude 6-methoxy-2-methylbenzo[b]thiophene-3-carbonyl chloride in THF (50 ml) was combined with a 2.0 M solution of CH3NH2 in THF (20 ml, 40 mmole). The resultant reaction mixture was stirred at ambient temperature for 3 hours. The solvent was removed by concentration, in vacuo, and the residue obtained was partitioned between H2O (50 ml) and CH2Cl2 (50 ml). The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×30 ml). The combined organic extracts were dried over Na2SO4 and concentrated, in vacuo, to give 0.8 g of an amber solid which was purified by silica gel chromatography. Elution with CH2Cl2: EtOAc (80:20) and evaporation of the appropriate fractions gave 693 mg (72%) of an off-white solid. 1H NMR (DMSO-d6) δ 8.15 (1H, q, J=4.6 Hz), 7.62 (1H, d, J=8.9 Hz), 7.47 (1H, d, J=2.4 Hz), 6.97 (1H, dd, J=2.4, 8.9 Hz), 3.79 (3H, s), 2.80 (3H, d, J=4.6 Hz), 2.53 (3H, s). Anal. Calcd. for C12H13NO2S: C, 61.25; H, 5.57; N, 5.95; S, 13.63. Found: C, 60.97; H, 5.56; N, 5.85; S, 13.44.

後処理

  1. customThe resultant reaction mixture
  2. customThe solvent was removed by concentration, in vacuo
  3. customthe residue obtained
  4. customwas partitioned between H2O (50 ml) and CH2Cl2 (50 ml)
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with CH2Cl2 (2×30 ml)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated, in vacuo

出典と根拠

ORDレコード
ord-b41a87a9df634250b1407ec123a74a40
出典データセット
uspto-grants-2006_05
特許番号
US07045528B2

反応ノート

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