Iodoethane → N-Ethylphenothiazine

HRID 1375307

반응식

HRID 1375307 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 (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).

후처리

  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)

출처 및 근거

ORD 기록
ord-243b4f4bd18e4e9b86c3f72c39e5d38d
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169520B2

연결된 노트

불러오는 중…