Imidazole → HCID 54365021, compound

HRID 1164168Notes

Reaction equation

[CH3:1][C:2]1([C:8]([OH:24])=[C:9]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.N1C=CN=C1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[CH3:1][C:2]1([CH:8]([O:24][C:30](=[O:32])[CH3:31])[C:9]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1

Participants

Reactant 3

HCID 795Imidazole

HCID 7918Acetic Anhydride

HCID 70534011HCID 70534011, compound

Product 1

HCID 54365021HCID 54365021, compoundYield 69.3%

Conditions

Temperature: 70 °C

Procedure

A mixture of 14 g (0.0378 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(3,4-dichlorophenyl)-propen-1-ol (Example 25), 1 g of imidazole and 80 g of acetic anhydride is stirred for 8 hours at 70° C. and then concentrated under reduced pressure. The residue is taken up in 300 ml of ether and stirred for half an hour with 100 ml of 6% strength sodium bicarbonate solution. The organic phase is dried over sodium sulfate and concentrated under reduced pressure, finally at 50° C. under 0.1 mbar. 10.8 g (69.3% of theory) of 1-(5-methyl-1,3-dioxan-5-yl)-1-acetoxy-2-(1,2,4-triazol-1-yl)-3-(3,4-dichlorophenyl)-prop-2-ene are obtained as a pale yellow resin.

Workup

concentrationconcentrated under reduced pressure
stirringstirred for half an hour with 100 ml of 6% strength sodium bicarbonate solution
dry with materialThe organic phase is dried over sodium sulfate
concentrationconcentrated under reduced pressure, finally at 50° C. under 0.1 mbar

Sources & evidence

ORD record: ord-7ae030f726b340fb8c91a59f6730b3d4
Source dataset: uspto-grants-1983_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04368066

Reaction notes

Loading…