1-Chloropropane → 1-(5-Methyl-1,3-dioxan-5-yl)-1-n-propoxy-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propane

HRID 851624Notes

Reaction equation

[CH3:1][C:2]1([CH:8]([OH:23])[CH:9]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.Cl[CH2:25][CH2:26][CH3:27].[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C:2]1([CH:8]([O:23][CH2:25][CH2:26][CH3:27])[CH:9]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:3][O:4][CH2:5][O:6][CH2:7]1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of 15.2 g (0.045 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-ol, 100 g of 1-chloropropane, 3 g of tetrabutylammonium bisulfate and 65 g of 50% strength sodium hydroxide solution is heated for 36 hours at 30° C., with vigorous stirring. 300 ml of water are then added and the batch is extracted with twice 150 ml of methylene chloride. The combined extracts are extracted by shaking with eight time 100 ml of water, dried over magnesium sulfate and evaporated down. The residue crystallizes after addition of 20 ml of petroleum ether and 5 ml of ether. 12 g (70.3%) of 1-(5-methyl-1,3-dioxan-5-yl)-1-n-propoxy-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propane are obtained as white crystals of melting point 94°-96° C.

Workup

extractionthe batch is extracted with twice 150 ml of methylene chloride
extractionThe combined extracts are extracted
dry with materialdried over magnesium sulfate
customevaporated down
customThe residue crystallizes
additionafter addition of 20 ml of petroleum ether and 5 ml of ether

Sources & evidence

ORD record: ord-d3b5e180bc6e47bda7fb9a5e6cfea4c9
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04385925

Reaction notes

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