Dichloromethane → (E)-3-Chloro-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methylbenzo[b]thiophene-7-methanamine hydrochloride

HRID 484543

反応式

HRID 484543 の反応式
Br[CH2:2][C:3]1[C:8]2[S:9][CH:10]=[C:11]([Cl:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[CH3:14][C:15]([CH3:24])([CH3:23])[C:16]#[C:17]/[CH:18]=[CH:19]/[CH2:20][NH:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].ClCCl>CS(C)=O>[ClH:12].[Cl:12][C:11]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:21]([CH2:20]/[CH:19]=[CH:18]/[C:17]#[C:16][C:15]([CH3:24])([CH3:23])[CH3:14])[CH3:22])[C:8]=2[S:9][CH:10]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 147805207-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 19917487(E)-N-methyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

生成物 1

HCID 6918069(E)-3-Chloro-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methylbenzo[b]thiophene-7-methanamine hydrochloride収率 77%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 0.34 g (1.3 mmol) of 7-bromomethyl-3-chlorobenzo[b]thiophene in 3 ml of dimethyl sulfoxide were added 0.246 g (1.31 mmol) of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)methylamine hydrochloride, and 0.27 g (1.95 mmol) of potassium carbonate -under ice cooling. The mixture was stirred for 19 hours at room temperature, poured into 40 ml of dichloromethane, washed with 30 ml×2 of water, and adjusted to pH 2 with 25 ml of water and 2N hydrochloric acid. The organic layer was separated, washed with 20 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and cooled to crystallize. The crystals were suspended in isopropylalcohol, filtered, washed with isopropyl alcohol and dried to obtain 0.37 g (yield: 77%) of the above identified compound as white crystalline powder. Melting point, IR and NMR data of the isolated compound agreed with those of Example 23 compound.

後処理

  1. washwashed with 30 ml×2 of water
  2. customThe organic layer was separated
  3. washwashed with 20 ml of saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. temperaturecooled
  7. customto crystallize
  8. filtrationfiltered
  9. washwashed with isopropyl alcohol
  10. customdried
  11. customto obtain 0.37 g (yield: 77%) of the

出典と根拠

ORDレコード
ord-08a18f1ae5d247fc8eef6a9cbe6cc1c3
出典データセット
uspto-grants-1993_07
特許番号
US05231183

関連ノート

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