Ammonium Hydroxide → HCID 69942017, compound

HRID 1358501Notes

Reaction equation

HRID 1358501 reaction equation
[OH:1][C@H:2]([C@H:4]([N:15]1[CH:19]=[N:18][C:17]([C:20]([O:22]CC)=O)=[N:16]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[Cl:14])[CH3:3].[OH-].[NH4+:26]>O1CCCC1.ClCCl>[OH:1][C@H:2]([C@H:4]([N:15]1[CH:19]=[N:18][C:17]([C:20]([NH2:26])=[O:22])=[N:16]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[Cl:14])[CH3:3]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 57070702HCID 57070702, compound

Product 1

HCID 69942017HCID 69942017, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 1-[(2S,3R)-2-hydroxy-5-(2,3-dichlorophenyl)-3-pentyl]-1,2,4-triazole-3-carboxylate (11.6 mg) and ammonium hydroxide (28% in water; 0.5 ml) in tetrahydrofuran (3 ml) was heated in a steel sealed tube at 120° C. overnight. The mixture was taken up in dichloromethane, washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (20:1) to give a white powder of 1-[(2S,3R)-2-hydroxy-5-(2,3-dichlorophenyl)-3-pentyl]-1,2,4-triazole-3-carboxamide (4.2 mg).

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (20:1)

Sources & evidence

ORD record
ord-bf245e7fdcf44cde89c69d607d24212b
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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