Carbon Tetrachloride → HCID 18925007, compound

HRID 1869093Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:33].[C:37]([C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][CH:45]=1)[NH2:42])#[CH:38]>ClCCCl>[ClH:33].[C:37]([C:39]1[CH:40]=[C:41]([NH:42][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:43]=[CH:44][CH:45]=1)#[CH:38]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Methyl-quinazolin-4-one (350 mg, 2.18 mmol) was added to a suspension of polymer-supported triphenylphosphine (from Fluka, 3.63 g of about 3 mmol P/g resin; 10.9 mmol) in a mixture of CCl4 (3.35 g, 21.80 mmol) and 1,2 dichloroethane (10 mL). The mixture was heated to 60° C. for 2 hours and then the polymer was removed by filtration and washed with dichloroethane. The filtrate was collected in a flask containing 3-ethynyl-aniline (0.644 g, 2.18 mmol) and concentrated to 5 mL by evaporation. After 4 hours reflux under N2, followed by cooling to 20° C., the title product was collected by filtration (551 mg; 86%; M.P. 256°-257° C.; LC-MS: 260 (MH+); anal. RP-HPLC RT: 4.41 min).

Workup

customthe polymer was removed by filtration
washwashed with dichloroethane
customThe filtrate was collected in a flask
concentrationconcentrated to 5 mL by evaporation
temperatureAfter 4 hours reflux under N2
temperatureby cooling to 20° C.
filtrationthe title product was collected by filtration (551 mg; 86%; M.P. 256°-257° C.; LC-MS: 260 (MH+); anal. RP-HPLC RT: 4.41 min)

Sources & evidence

ORD record: ord-605bed10bb62461889f0f038875b5c68
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE041065E1

Reaction notes

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