Fumaric Acid → HCID 14536547, compound

HRID 728707Notes

Reaction equation

HRID 728707 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:9]([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]([CH2:35][CH3:36])[CH2:33][CH3:34])[C:18]=2[CH:17]=1)=[O:15])[CH2:10][CH2:11][CH3:12]>CC(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:9]([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]([CH2:33][CH3:34])[CH2:35][CH3:36])[C:18]=2[CH:17]=1)=[O:15])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 14536546HCID 14536546, compound

Product 1

HCID 14536547HCID 14536547, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
25 °C

Procedure

Fumaric acid (0.13 g) dissolved in 2-propanol (5 cc) under reflux is added to a solution of N-butyl-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarboxamide (0.46 g) in boiling 2-propanol (5 cc). Crystallization is primed by scratching, and the mixture is stirred for 5 hours at 25° C. The crystals are filtered off on sintered glass, washed with ice-cold 2-propanol (2×3 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) to give N-butyl-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarboxamide fumarate (0.34 g), m.p. 129° C.

Workup

  1. temperatureunder reflux
  2. customCrystallization
  3. filtrationThe crystals are filtered off on sintered glass
  4. washwashed with ice-cold 2-propanol (2×3 cc)
  5. customdried under reduced pressure (5 mm Hg; 0.7 kPa)

Sources & evidence

ORD record
ord-8c7bbefd17654262aea96ce8e4733346
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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