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

HRID 1660342ノート

反応式

HRID 1660342 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-91da242007414d8492bb4122ea2a5751
出典データセット
uspto-grants-1981_12
特許番号
US04307234

反応ノート

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