Tetrahydrofuran → HCID 20339459, compound

HRID 1395549Notes

Reaction equation

HRID 1395549 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.O1CCCC1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O>[NH2:9][C:3]1[N:4]=[C:5]([NH:8][C:21](=[O:22])[O:23][CH2:24][CH3:25])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 122639943-chloropyridine-2,6-diamine

Product 1

HCID 20339459HCID 20339459, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-chloro-2,6-diaminopyridine (129 g. 0.9 mole) in 1000 ml. of tetrahydrofuran and 250 ml. of water containing sodium bicarbonate (84 g., 1.0 mole) is stirred at 0° C. while adding ethyl chloroformate (114 g. 1.05 mole) dropwise over 1/2 hour. The mixture is stirred at 0° C. over night. The dark solution is filtered through activated carbon and the organic layer of the filtrate is separated, dried and concentrated in vacuo. The residual oil is taken up in ether, washed with 5 N sodium hydroxide and with saturated sodium chloride solution, dried and concentrated in vacuo. A light amber oil (162 g.) which solidifies when triturated in petroleum ether is obtained. The solid is purified by extracting into boiling hexane (10×300 ml) and cooling the extracts to give 131.6 g. of white solid, m.p. 66°-70°.

Workup

  1. stirringThe mixture is stirred at 0° C. over night
  2. filtrationThe dark solution is filtered through activated carbon
  3. customthe organic layer of the filtrate is separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. washwashed with 5 N sodium hydroxide and with saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customtriturated in petroleum ether
  10. customis obtained
  11. customThe solid is purified
  12. extractionby extracting
  13. temperaturecooling the extracts
  14. customto give 131.6 g

Sources & evidence

ORD record
ord-d653c2260bad4f5bbd49442421277068
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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