Dimethyl Sulfoxide → HCID 15036432, compound

HRID 1534110Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:9]#[N:10])=[CH:4][CH:3]=1.N1C=CN=N1.[K].CS(C)=O.BrCC(C#N)(C1C=CC(Cl)=CC=1)CCC1C=CC=C([C:46]([F:49])([F:48])[F:47])C=1>CCOCC.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([C:46]([F:49])([F:48])[F:47])[CH:24]=2)([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 500 ml 1 neck round bottom flask was charged with 10.7 gms of potassium triazole (0.10 mole, 4.0 eq.), 75 ml of DMSO and 1-bromo-2-cyano-2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)butane (10.4 gms, 0.025 mole, 1.0 eq.). The reaction was heated at 80° C. overnight and then quenched by adding 1 liter of H2O and extracted three times with 200 ml of ether. The combined ether extracts were washed with water and brine, then dried and rotovaped to give a crude product which was slurried in ether:hexane (1:1). A solid formed which was washed with hexane and gave 5.0 gms of a light yellow solid having a melting point of 118°-121° C. (47% yield).

Workup

customquenched
additionby adding 1 liter of H2O
extractionextracted three times with 200 ml of ether
washThe combined ether extracts were washed with water and brine
customdried
customto give a crude product which
customA solid formed which
washwas washed with hexane

Sources & evidence

ORD record: ord-303150d41c5e4f078c8b216c01167b0c
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05087635

Reaction notes

Loading…