Fumaric Acid → HCID 15096223, compound

HRID 1109548Notes

Reaction equation

HRID 1109548 reaction equation
C(O)(=O)/C=C/C(O)=[O:5].[CH3:9][C:10]1[CH:41]=[CH:40][CH:39]=[CH:38][C:11]=1[CH2:12][NH:13][C:14]([C:16]1[CH:29]=[CH:28][C:27]2[S:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:30]([CH3:37])[CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:18]=2[CH:17]=1)=S>C(O)(=O)C>[CH3:9][C:10]1[CH:41]=[CH:40][CH:39]=[CH:38][C:11]=1[CH2:12][NH:13][C:14]([C:16]1[CH:29]=[CH:28][C:27]2[S:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:30]([CH3:37])[CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:18]=2[CH:17]=1)=[O:5]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 15925313HCID 15925313, compound

Product 1

HCID 15096223HCID 15096223, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

Fumaric acid (0.7 g) and mercuric acetate (2.5 g) are added in the course of 20 minutes to a solution of N-(2-methylbenzyl)-10[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (3.8 g) in acetic acid (30 cc), and the mixture obtained is stirred for 12 hours at a temperature in the region of 20° C. The black suspension obtained is filtered on sintered glass plugged with Celite and the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with ethyl acetate (100 cc) and the organic phase is washed successively with normal sodium hydroxide (2×20 cc) and distilled water (2×20 cc) and with saturated aqueous sodium chloride solution (20 cc) and dried over magnesium sulphate. After filtration, the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and N-(2-methylbenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (3.2 g), is thereby obtained in the form of a yellow oil, which is used subsequently without further treatment.

Workup

  1. customthe mixture obtained
  2. customThe black suspension obtained
  3. filtrationis filtered on sintered glass
  4. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  5. washthe organic phase is washed successively with normal sodium hydroxide (2×20 cc)
  6. distillationdistilled water (2×20 cc)
  7. dry with materialwith saturated aqueous sodium chloride solution (20 cc) and dried over magnesium sulphate
  8. filtrationAfter filtration
  9. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-97b875e1d73b48b188e377661607a1f0
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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