Fumaric Acid → HCID 20074838, compound

HRID 704206Notes

Reaction equation

HRID 704206 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH:9]1([CH2:13][NH:14][C:15]([C:17]2[CH:30]=[CH:29][C:28]3[S:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH:31]([CH3:38])[CH2:32][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[C:19]=3[CH:18]=2)=[S:16])[CH2:12][CH2:11][CH2:10]1>CC(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH:9]1([CH2:13][NH:14][C:15]([C:17]2[CH:30]=[CH:29][C:28]3[S:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH:31]([CH3:38])[CH2:32][N:33]4[CH2:34][CH2:35][CH2:36][CH2:37]4)[C:19]=3[CH:18]=2)=[S:16])[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 20074839HCID 20074839, compound

Product 1

HCID 20074838HCID 20074838, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of fumaric acid (0.58 g) in 2-propanol (14 cc) under reflux is added to a solution of N-cyclobutylmethyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (2.19 g) in 2-propanol (16 cc) under reflux. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the residue is taken up with stirring for 16 hours with isopropyl ether (70 cc). The suspension obtained is filtered and the solid is dried under reduced pressure (5 mm Hg; 4 kPa) at 50° C. and dissolved in 2-propanol under reflux (50 cc). After cooling, the product crystallizes and stirring is continued for 16 hours at 20° C. The crystals are filtered off and dried under reduced pressure (5 mm Hg; 4 kPa) at 50° C. N-Cyclobutylmethyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide fumarate, L series (1.52 g) is thereby obtained in the form of yellow crystals, m.p. 194° C.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  4. customThe suspension obtained
  5. filtrationis filtered
  6. customthe solid is dried under reduced pressure (5 mm Hg; 4 kPa) at 50° C.
  7. dissolutiondissolved in 2-propanol
  8. temperatureunder reflux (50 cc)
  9. temperatureAfter cooling
  10. customthe product crystallizes
  11. stirringstirring
  12. waitis continued for 16 hours at 20° C
  13. filtrationThe crystals are filtered off
  14. customdried under reduced pressure (5 mm Hg; 4 kPa) at 50° C

Sources & evidence

ORD record
ord-b2bbfd926fcb4b6bbf6b2002bb464bfa
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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