2,3-Dihydroxybutanedioic Acid → HCID 70363399, compound

HRID 1089104Notes

Reaction equation

HRID 1089104 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=3[N:11]([CH2:12][CH2:13][CH2:14]Cl)[C:4]=2[CH:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23].[I-].[Na+].[C:28]([OH:37])(=[O:36])[CH:29]([CH:31]([C:33]([OH:35])=[O:34])O)O.C(O)(=O)/C=C\C(O)=O>C(O)(C)C.O.C(C(C)=O)C>[C:28]([OH:37])(=[O:36])/[CH:29]=[CH:31]\[C:33]([OH:35])=[O:34].[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=3[N:11]([CH2:12][CH2:13][CH2:14][NH:25][CH:22]([CH3:24])[CH3:23])[C:4]=2[CH:3]=1

Participants

9

Reactant 5

HCID 8752,3-Dihydroxybutanedioic AcidHCID 5238Sodium IodideHCID 6363IsopropylamineHCID 444266Maleic AcidHCID 23287875HCID 23287875, compound

Product 1

HCID 70363399HCID 70363399, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 32.4 g. (0.10 moles) of 2-chloro-12-(3-chloropropyl)-12H-dibenzo[d,g][1,3,6]dioxazocine prepared by the method of Example 1, 11.8 g. (0.20 moles) of isopropyl amine, 7.5 g. of sodium iodide and 200 ml. of methyl ethyl ketone is stirred under reflux for 20 hours. Thereafter the solvent is removed in vacuo, 100 ml. of benzene are added to the residue and the mixture obtained is washed with water. Thereafter 37.5 g. (0.25 moles) of tartaric acid and 150 ml. of water are added to the organic phase and the reaction mixture is stirred for 30 minutes. The aqueous phase is separated, 150 ml. of methylene chloride are added thereto and the pH is adjusted to 10 by using aqueous ammonia. The organic phase is separated and the solvent is removed. The residue is dissolved in 100 ml. of isopropanol and a solution of 9.5 g (0.82 moles) of maleic acid is added thereto. The precipitated white product is filtered off, dried and recrystallized from isopropanol. There are obtained 32.4 g. (70.0%) of the title product, melting at 126° to 129° C.

Workup

  1. additionA mixture of 32.4 g
  2. temperatureunder reflux for 20 hours
  3. customThereafter the solvent is removed in vacuo, 100 ml
  4. additionof benzene are added to the residue
  5. customthe mixture obtained
  6. washis washed with water
  7. customThe aqueous phase is separated
  8. additionof methylene chloride are added
  9. customThe organic phase is separated
  10. customthe solvent is removed
  11. dissolutionThe residue is dissolved in 100 ml
  12. filtrationThe precipitated white product is filtered off
  13. customdried
  14. customrecrystallized from isopropanol
  15. customThere are obtained 32.4 g

Sources & evidence

ORD record
ord-d6ce08b2baea4b93bf6c851c9c21e168
Source dataset
uspto-grants-1990_10
Patent number
US04965259

Reaction notes

Loading…