Sulfur Dioxide → 2-Acetyl-8-chlorosulfonyl-7-chloro-1,2,3,4-tetrahydroisoquinoline

HRID 461487

反応式

HRID 461487 の反応式
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7](N)[C:8]([Cl:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].N([O-])=O.[Na+].N(O)=O.[Cl-:23].[Mg+2].[Cl-].[S:26](=[O:28])=[O:27]>Cl.O.C(O)(=O)C>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([S:26]([Cl:23])(=[O:28])=[O:27])[C:8]([Cl:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

参加物

9

反応物 5

HCID 1119Sulfur DioxideHCID 24529Nitrous Acid2 回HCID 5360315Magnesium ChlorideHCID 205232142-Acetyl-8-amino-7-chloro-1,2,3,4-tetrahydroisoquinolineHCID 23668193Sodium Nitrite2 回

生成物 1

HCID 128380412-Acetyl-8-chlorosulfonyl-7-chloro-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回

反応条件

温度
30 °C

実験手順

2-Acetyl-8-amino-7-chloro-1,2,3,4-tetrahydroisoquinoline (0.04 mole) in concentrated hydrochloric acid (8.4 ml.) is cooled to 3° C. and treated with sodium nitrite (0.044 mole) dissolved in water (6 ml.). After stirring for 30 minutes, the reaction is tested for nitrous acid with starch/iodide paper. If the test for nitrous acid is negative, more sodium nitrite is added in small portions with stirring over a period of time until the test is positive. When a positive reaction is obtained, magnesium chloride (0.032 mole) is added and the resulting mixture is added to a mixture of acetic acid (40 ml.) saturated with sulfur dioxide and cuprous chloride dihydrate (0.0129 mole) maintained at 30° C and stirred. After about 30 minutes, the mixture is diluted with water (60 ml.) and extracted with ether. The extract is then washed with dilute aqueous sodium bicarbonate/sodium carbonate solution at pH 8-9, then with water, and dried over sodium sulfate. The ether is evaporated to yield 2-acetyl-8-chlorosulfonyl- 7-chloro-1,2,3,4-tetrahydroisoquinoline. 2-Acetyl-8-chlorosulfonyl-7-chloro-1,2,3,4-tetrahydroisoquinoline (0.022 mole) is treated with concentrated ammonium hydroxide (30 ml.) with cooling. The resulting solid is filtered off and washed with water to give 2-acetyl-7-chloro-8-sulfamyl-1,2,3,4-tetrahydroisoquinoline.

後処理

  1. stirringwith stirring over a period of time until the test
  2. customWhen a positive reaction
  3. customis obtained
  4. stirringstirred
  5. waitAfter about 30 minutes
  6. extractionextracted with ether
  7. washThe extract is then washed with dilute aqueous sodium bicarbonate/sodium carbonate solution at pH 8-9
  8. dry with materialwith water, and dried over sodium sulfate
  9. customThe ether is evaporated

出典と根拠

ORDレコード
ord-5bd340bfe352481c9c204a8a20fba69a
出典データセット
uspto-grants-1977_12
特許番号
US04062961

関連ノート

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