2,3-Dihydroxybutanedioic Acid → HCID 88527765, compound

HRID 1460551Notes

Reaction equation

HRID 1460551 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:13][CH2:14]Cl)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:16]1([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CO>[C:34]([CH:32]([CH:30]([C:29]([OH:38])=[O:37])[OH:31])[OH:33])([OH:36])=[O:35].[NH2:1][C:2]1[S:3][C:4]([CH2:13][CH2:14][N:25]2[CH2:24][CH:23]=[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:27][CH2:26]2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 962WaterHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 4152550HCID 4152550, compound

Product 1

HCID 88527765HCID 88527765, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

20 mmol of 2-amino-5-(2-chloroethyl)-4-phenylthiazole and 20 mmol of 4-phenyl-1,2,3,6-tetrahydropyridine were thoroughly mixed and were heated under an N2 atmosphere at 120° C. until conversion was complete, which was the case after 20 minutes. After cooling, the solidified melt was stirred with water, the oily solid residue was separated off and stirred thoroughly with methanol and the solid was filtered off under suction. The filter residue was partitioned in 2 N NaOH/CH2Cl2 and the organic phase was separated off, dried and evaporated down. The residue was dissolved in methanol while hot, one equivalent of tartaric acid was added and the precipitated solid was filtered off under suction and purified by recrystallization from ethyl acetate.

Workup

  1. customafter 20 minutes
  2. temperatureAfter cooling
  3. customthe oily solid residue was separated off
  4. filtrationthe solid was filtered off under suction
  5. customThe filter residue was partitioned in 2 N NaOH/CH2Cl2
  6. customthe organic phase was separated off
  7. customdried
  8. customevaporated down
  9. additionwas added
  10. filtrationthe precipitated solid was filtered off under suction
  11. custompurified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5aae88503a7249d39c480b52c37343cb
Source dataset
uspto-grants-1991_12
Patent number
US05071864

Reaction notes

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