Phosphorus oxychloride → 5-(2-Chloroethyl)-1-(chloromethyl)-4-methylpyrimido[1,6-a]indole

HRID 1660342노트

반응식

HRID 1660342 반응식
[Cl:1][CH2:2][C:3]([NH:5][CH2:6][C:7]1([CH3:20])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH2:10][CH2:9]O1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=O.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]2[C:3]([CH2:2][Cl:1])=[N:5][CH:6]=[C:7]([CH3:20])[C:12]=12

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 127081932-Chloro-N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]acetamide

생성물 1

HCID 127081975-(2-Chloroethyl)-1-(chloromethyl)-4-methylpyrimido[1,6-a]indole

실험 절차

A mixture of 2-chloro-N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamide (9.0 g, described in Example 8) and phosphorus oxychloride (200 ml) is refluxed for 60 minutes and evaporated slowly to dryness under reduced pressure (10 mm Hg, the final bath temperature 140° C.). The residue is dissolved in chloroform and the solution is washed quickly with ice-cold 5% solution of sodium hydroxide, dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed through a column of silica gel (300 g) using chloroform. The eluates are evaporated and the residue is crystallized from ethyl acetate to obtain the title compound (5.5 g); mp 160°-161° C., nmr(CDCl3) δ2.53(s), 3.62(m), 4.94(s) and 7.10-8.20(m).

후처리

  1. temperatureis refluxed for 60 minutes
  2. customevaporated slowly to dryness under reduced pressure (10 mm Hg
  3. customtemperature 140° C.
  4. dissolutionThe residue is dissolved in chloroform
  5. washthe solution is washed quickly with ice-cold 5% solution of sodium hydroxide
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is chromatographed through a column of silica gel (300 g)
  10. customThe eluates are evaporated
  11. customthe residue is crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-91da242007414d8492bb4122ea2a5751
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307234

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