Acetic Acid → HCID 13193050, compound

HRID 371250Notes

Reaction equation

HRID 371250 reaction equation
[O:1]=[CH:2][C:3]([Cl:6])([Cl:5])[Cl:4].[CH3:7][C:8]1([C:11](=[O:18])[CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:10][CH2:9]1.C(O)(=O)C.C([O-])(=O)C.[Na+]>CCOCC.O>[Cl:4][C:3]([Cl:6])([Cl:5])[CH:2]([OH:1])[CH:12]([N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[C:11]([C:8]1([CH3:7])[CH2:9][CH2:10]1)=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6407ChloralHCID 517045Sodium AcetateHCID 12760574HCID 12760574, compound

Product 1

HCID 13193050HCID 13193050, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
45 °C

Procedure

9.2 g (0.0625 mol) of chloral were added dropwise to 8.3 g (0.05 mol) of 1-methyl-1-(1,2,4-triazol-1-yl-acetyl)-cyclopropane, 20 ml of glacial acetic acid and 13.6 g (0.1 mol) of sodium acetate, the internal temperature increasing to approx. 45° C. The reaction mixture was stirred overnight at 80° C. and was thereafter cooled to room temperature and stirred with a mixture of 100 ml of water and 100 ml of ether. The resulting solid was filtered off under suction and recrystallized from methanol. 3.1 g (20% of theory) of 1,1,1-trichloro-2-hydroxy-3-(1,2,4-triazol-1yl)-4-(1-methylcycloprop-1-yl)-butan-4-one of melting point 216° to 218° C. were obtained.

Workup

  1. temperaturewas thereafter cooled to room temperature
  2. filtrationThe resulting solid was filtered off under suction
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7eddf2419ed24ee9b1c0523957274bf2
Source dataset
uspto-grants-1985_07
Patent number
US04530715

Reaction notes

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