Tetrahydrofuran → HCID 23350231, compound

HRID 2057860Notes

Reaction equation

HRID 2057860 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10](OCC)[CH:11]=C=O)=[CH:4][C:3]=1[N:17]1[C:25](=[O:26])[N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C:19]2=[N:18]1.[O:27]1CCC[CH2:28]1.[BH4-].[Na+].[Cl-].[Li+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH2:28][OH:27])[CH3:11])=[CH:4][C:3]=1[N:17]1[C:25](=[O:26])[N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C:19]2=[N:18]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium Chloride3×HCID 4311764Sodium borohydride3×HCID 86737096HCID 86737096, compound

Product 1

HCID 23350231HCID 23350231, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0 Parts of 2-[2,4-dichloro-5-(1-ethoxy-carbonylethoxy)-phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A] pyridin-3(2H)-one prepared as described in Example 5 in 75 parts of tetrahydrofuran was treated with 0.3 part of sodium borohydride and 0.3 part of lithium chloride. The reaction was heated to 40° for 6 hours. After this period 0.6 part of sodium borohydride and 0.5 parts of lithium chloride were added and the reaction was then stirred for 12 hours at room temperature. The reaction was heated to reflux and an additional 3.0 parts of sodium borohydride and 2.8 parts of lithium chloride were added in small portions over 48 hours. The mixture was cooled and added slowly to 100 parts of water whereby some foaming occurred. The product was extracted three times with 200 parts of ether. The ether was then extracted twice with 100 parts of water. The ether layer was dried with sodium sulfate. The ether was stripped on a rotary evaporator at reduced pressure. The residue was triturated with methylene chloride yielding 0.35 part of a tan solid with m.p. 54°-57°.

Workup

  1. temperatureThe reaction was heated to 40° for 6 hours
  2. temperatureThe reaction was heated
  3. temperatureto reflux
  4. temperatureThe mixture was cooled
  5. extractionThe product was extracted three times with 200 parts of ether
  6. extractionThe ether was then extracted twice with 100 parts of water
  7. dry with materialThe ether layer was dried with sodium sulfate
  8. customThe ether was stripped on a rotary evaporator at reduced pressure
  9. customThe residue was triturated with methylene chloride yielding 0.35 part of a tan solid with m.p. 54°-57°

Sources & evidence

ORD record
ord-ed8f650ac5ce4f028a20edd386658d2a
Source dataset
uspto-grants-1980_07
Patent number
US04213773

Reaction notes

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