Methyl chloroformate → HCID 70447670, compound

HRID 358346Notes

Reaction equation

HRID 358346 reaction equation
[NH2:1][C:2]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])([CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)[CH2:3][N:4]1[CH:8]=[N:7][CH:6]=[N:5]1.[H-].[Na+].Cl[C:26]([O:28][CH3:29])=[O:27]>O1CCCC1>[OH2:27].[N:10]1([CH2:9][C:2]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])([NH:1][C:26]([O:28][CH3:29])=[O:27])[CH2:3][N:4]2[CH:8]=[N:7][CH:6]=[N:5]2)[CH:14]=[N:13][CH:12]=[N:11]1.[N:10]1([CH2:9][C:2]([NH:1][C:26]([O:28][CH3:29])=[O:27])([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:3][N:4]2[CH:8]=[N:7][CH:6]=[N:5]2)[CH:14]=[N:13][CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 20448705HCID 20448705, compound

Product 1

HCID 70447670HCID 70447670, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-1,3-bis(1H-1,2,4-triazol-1-yl)-2-(2,4-dichlorophenyl)propane (0.234 g, 0.7 mmole) was added to a suspension of oil-free sodium hydride (27 mg, 1.125 mmole) in dry tetrahydrofuran (5 ml) and the mixture was stirred at room temperature for 1 hour. Methyl chloroformate (0.104 g, 1.1 mmole) was then added and the mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue dissolved in chloroform (25 ml) and then washed with water (10 ml). The organic phase was dried (MgSO4), filtered and evaporated and the residue was recrystallized from ethyl acetate to furnish the title compound as a colorless solid (48 mg, 17%), m.p. 171°-2°.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in chloroform (25 ml)
  4. washwashed with water (10 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f616d378d0ab49a583f91b1320dd7252
Source dataset
uspto-grants-1984_08
Patent number
US04466974

Reaction notes

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