Thionyl Chloride → HCID 15925380、化合物

HRID 704239ノート

反応式

HRID 704239 の反応式
S(Cl)(Cl)=O.Cl.[N:6]1([CH2:11][CH:12]([N:14]2[C:27]3[CH:26]=[C:25]([C:28]([OH:30])=O)[CH:24]=[CH:23][C:22]=3[S:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH3:13])[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH2:36].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OC(C)C)(C)C>[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH:36][C:28]([C:25]1[CH:24]=[CH:23][C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH:12]([CH3:13])[CH2:11][N:6]3[CH2:7][CH2:8][CH2:9][CH2:10]3)[C:27]=2[CH:26]=1)=[O:30]

参加物

7

反応物 4

HCID 24386Thionyl ChlorideHCID 77802Benzenemethanamine, 3-chloro-HCID 516892Sodium BicarbonateHCID 1453664010-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride

生成物 1

HCID 15925380HCID 15925380、化合物収率 60.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 7914Diisopropyl Ether溶媒

反応条件

温度
25 °C

実験手順

Thionyl chloride (3.6 cc) is added to a suspension, cooled to 5° C., of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride (2.7 g) in methylene chloride (70 cc). The suspension is stirred for 3 hours at 25° C. and then concentrated to dryness at 30° C. under reduced pressure (30 mm Hg; 4 kPa) to give a yellow residue which is taken up with methylene chloride (50 cc) at 5° C. 3-Chlorobenzylamine (6.9 g) is added and the mixture is stirred for 12 hours at 25° C., and saturated sodium bicarbonate solution (150 cc) is then added. The mixture is extracted with ethyl acetate (2×100 cc). The organic phase is washed successively with distilled water (100 cc) and with brine (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give a brown oil which is purified by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica (0.06-0.2 mm), eluting with methylene chloride (1 liter) and collecting 40-cc fractions. Fractions 12 to 24 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a cream-coloured solid which is taken up in isopropyl ether (20 cc). The solid is separated by filtration, washed with isopropyl ether (2×5 cc) and dried at 40° C. under reduced pressure (1 mm Hg; 0.13 kPa). N-(3-Chlorobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (2 g) is obtained in the form of a yellow solid, m.p. approximately 80° C.

後処理

  1. concentrationconcentrated to dryness at 30° C. under reduced pressure (30 mm Hg; 4 kPa)
  2. customto give a yellow residue which
  3. stirringthe mixture is stirred for 12 hours at 25° C.
  4. extractionThe mixture is extracted with ethyl acetate (2×100 cc)
  5. washThe organic phase is washed successively with distilled water (100 cc) and with brine (100 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa)
  9. customto give a brown oil which
  10. customis purified by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica (0.06-0.2 mm)
  11. washeluting with methylene chloride (1 liter)
  12. customcollecting 40-cc fractions
  13. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  14. customto give a cream-coloured solid which
  15. customThe solid is separated by filtration
  16. washwashed with isopropyl ether (2×5 cc)
  17. customdried at 40° C. under reduced pressure (1 mm Hg; 0.13 kPa)

出典と根拠

ORDレコード
ord-218ec5fb77c24e9390bb544f663fb770
出典データセット
uspto-grants-1991_01
特許番号
US04985419

反応ノート

読み込み中…