Sodium hydride → 3-(7-(2-Chloroethoxy)-6-methoxyquinazolin-4-ylthio)aniline

HRID 631561ノート

反応式

HRID 631561 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][Cl:27])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1>C1COCC1>[Cl:27][CH2:26][CH2:25][O:24][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([S:8][C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=3)[NH2:1])=[N:13][CH:14]=[N:15]2)=[CH:20][C:19]=1[O:22][CH3:23]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 315773-AminothiophenolHCID 596829074-Chloro-7-(2-chloroethoxy)-6-methoxyquinazoline

生成物 1

HCID 668763233-(7-(2-Chloroethoxy)-6-methoxyquinazolin-4-ylthio)aniline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a round bottomed flask 3-aminothiophenol (279 mg, 2.23 mmol) was dissolved in 10 mL of dry THF. To this solution was added sodium hydride, 60% suspension in mineral oil, (86 mg, 2.23 mmol) and the reaction stirred for 30 minutes. 4-chloro-7-(2-chloro-ethoxy)-6-methoxy-quinazoline (610 mg, 2.23 mmol) from Example 35A was added as a 10 mL solution in THF, and the reaction stirred overnight at room temperature. The solution was then concentrated to dryness, and partitioned between ethyl acetate and water, and extracted with an additional portion of ethyl acetate. The extracts were combined, dried with magnesium sulfate, filtered, and concentrated to give 3-(7-(2-chloroethoxy)-6-methoxyquinazolin-4-ylthio)aniline as a yellow solid weighing 600 mg. 1H NMR (300 MHz, DMSO-d6) δ 8.70 (s, 1H), 7.47 (d, 2H), 7.17 (m, 1H), 6.83 (s, 1H), 6.72 (m, 2H), 4.51 (m, 2H), 4.05 (m, 3H), 3.89 (s, 3H), 3.51 (bs, 2H); LC-MS (ESI) m/z 362 (M+H)+.

後処理

  1. stirringthe reaction stirred overnight at room temperature
  2. concentrationThe solution was then concentrated to dryness
  3. custompartitioned between ethyl acetate and water
  4. extractionextracted with an additional portion of ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0643646ca29244c284e53f03e1eb1f79
出典データセット
uspto-grants-2016_04
特許番号
US09320739B2

反応ノート

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