Iodoethane → N-Ethylphenothiazine

HRID 268576

반응식

HRID 268576 반응식
[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]

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 7108PhenothiazineHCID 14797Potassium Hydroxide

생성물 1

HCID 219178N-Ethylphenothiazine

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매

실험 절차

A mixture of 10 g (0.05 mol) of phenothiazine (obtained from Fluka), 11.7 g (0.075 mol) of iodoethane (obtained from Aldrich), 4.2 g (0.075 mol) of potassium hydroxide and 0.25 g of tetra-n-butylammonium hydrogen sulfate (obtained from Aldrich) in 200 ml of dry toluene was refluxed for 24 hours. After cooling, the reaction mixture was filtered and the solvent was evaporated. The product was recrystallized from methanol. The yield of 10-ethylphenothiazine (C14H13NS, FW=227.33) was 90%. The melting point of the product was 103-104° C. The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (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).

후처리

  1. temperaturewas refluxed for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent was evaporated
  5. customThe product was recrystallized from methanol
  6. customwas 103-104° C

출처 및 근거

ORD 기록
ord-5dca1ffcee9c4e1fac40ef9667593d59
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07445877B2

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