Thionyl Chloride → HCID 15925380, 화합물

HRID 704239

반응식

HRID 704239 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 15925380HCID 15925380, 화합물수율 60.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 7914Diisopropyl Ether용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-218ec5fb77c24e9390bb544f663fb770
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985419

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