Tetrahydrofuran → HCID 13960815, compound

HRID 2308814Notes

Reaction equation

HRID 2308814 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[N:6]=1)=[O:4].[O:18]1CC[CH2:20][CH2:19]1.C1(N=C=NC2CCCCC2)CCCCC1>C(O)CO>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([O:13][CH2:20][CH2:19][OH:18])=[O:12])[CH:8]=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 13960809HCID 13960809, compound

Product 1

HCID 13960815HCID 13960815, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

2,6-Bis(N-methylcarbamoyl)pyridine-4-carboxylic acid (2.3 g) prepared in Example 2 was mixed with 50 ml of tetrahydrofuran and 3.1 g of ethylene glycol. After addition of 2.5 g of dicyclohexyl carbodiimide, the mixture was stirred at room temperature overnight. The mixture was then evaporated and the residue was purified by a column chromatography on silica gel, and recrystallized from dimethylformamide/benzene to give 0.3 g of 2-hydroxyethyl 2,6-bis(N-methylcarbamoyl)pyridine-4-carboxylate. m.p. 214°-215° C.

Workup

  1. customThe mixture was then evaporated
  2. customthe residue was purified by a column chromatography on silica gel
  3. customrecrystallized from dimethylformamide/benzene

Sources & evidence

ORD record
ord-75fea895c798421b9013f241f4503b98
Source dataset
uspto-grants-1987_09
Patent number
US04691018

Reaction notes

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