Iodoethane → N-Ethylphenothiazine

HRID 1375307

反応式

HRID 1375307 の反応式
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[CH2:16][CH3:17].[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:16]([N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:17]

参加物

6

反応物 3

HCID 6340IodoethaneHCID 7108PhenothiazineHCID 14797Potassium Hydroxide

生成物 1

HCID 219178N-Ethylphenothiazine

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒

実験手順

A mixture of 10 g (0.05 mol) of phenothiazine (from Fluka), 11.7 g (0.075 mol) of iodoethane (from Aldrich), 4.2 g (0.075 mol) of potassium hydroxide, and 0.25 g of tetra-n-butylammonium hydrogen sulfate (from Aldrich) in 200 ml of dry toluene was refluxed for 24 hrs. The cooled reaction mixture was filtered and the solvent was evaporated. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine was 10.2 g (90%). The product had a melting point of 103–104° C. (recrystallized from methanol). A 1H NMR spectrum yielded the following results (100 MHz, CDCl3, δ, ppm): 1.40 (t, J=7.0 Hz, 3H, CH3); 3.90 (q, J=7.0 Hz, 2H, CH2); 6.78–7.32 (m, 8H, Ar).

後処理

  1. temperaturewas refluxed for 24 hrs
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customthe solvent was evaporated
  5. customThe product was recrystallized from methanol
  6. customa melting point of 103–104° C. (recrystallized from methanol)
  7. customA 1H NMR spectrum yielded the
  8. customfollowing results (100 MHz, CDCl3, δ, ppm)

出典と根拠

ORDレコード
ord-243b4f4bd18e4e9b86c3f72c39e5d38d
出典データセット
uspto-grants-2007_01
特許番号
US07169520B2

関連ノート

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