Ammonium Chloride → HCID 14747543, compound

HRID 1199596Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:15][CH:16]([CH3:25])[C:17]([C:19]1[CH:20]=[N:21][CH:22]=[N:23][CH:24]=1)=[O:18].[Cl-].[NH4+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:17]([OH:18])([C:19]2[CH:20]=[N:21][CH:22]=[N:23][CH:24]=2)[CH:16]([CH3:25])[CH3:15])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -35 °C

Procedure

1(4'-Chlorophenyl)ethyne (1.43g:0.01 mole) was dissolved in tetrahydrofuran (10 ml) under nitrogen and cooled to -35° C. Butyllithium was added (6.5 ml of 1.6M solution:0.0104 mole) causing the colour to change. The mixture was stirred for 1/2 hour during which time it thickened and the colour changed to pink (from purple). Addition of a solution of chlorotanium triisopropoxide (10.6 ml or a 1 molar solution:0.0106 mole) caused the colour to change to yellow and the mixture was stirred for 20 minutes. The mixture was cooled to -60° C. and a solution of 2-methyl 1(pyrimidin-5-yl)propan-1-one in tetrahydrofuran (10 ml) was added and the reaction mixture allowed to warm up to room temperature within the cold bath. A solution of ammonium chloride in water (20%) was added and the mixture filtered. The aqueous was extracted with ethyl acetate (×3), washed (with water then brine), dried and the solvent removed in vacuo. The product was passed through silica (in ether) and then titurated with pentane and ether (0.467g: off white solid).

Workup

stirringwas stirred for 20 minutes
temperatureThe mixture was cooled to -60° C.
temperatureto warm up to room temperature within the cold bath
filtrationthe mixture filtered
extractionThe aqueous was extracted with ethyl acetate (×3)
washwashed (with water
dry with materialbrine), dried
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-f8e3967d4f2a4cdc97b63718399ec46d
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04902332

Reaction notes

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