Benzenamine, 3-ethynyl- → 6,7-Bis(2-chloroethoxy)-N-(3-ethynylphenyl)quinazolin-4-amine--hydrogen chloride (1/1)

HRID 1869083Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][CH2:18][Cl:19])=[C:9]([O:12][CH2:13][CH2:14][Cl:15])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:20]([C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])#[CH:21]>C(O)(C)C>[ClH:1].[Cl:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:16][CH2:17][CH2:18][Cl:19])[N:5]=[CH:4][N:3]=[C:2]2[NH:25][C:24]1[CH:26]=[CH:27][CH:28]=[C:22]([C:20]#[CH:21])[CH:23]=1

Participants

Conditions

Temperature: 20 °C

Procedure

4-Chloro-6,7-bis-(2-chloro-ethoxy)-quinazoline (600 mg, 1.87 mmol) and 3-ethynyl-aniline (219 mg, 1.87 mmol) were reacted in refluxing isopropanol (15 mL) under an atmosphere of N2 for 2.5 hours. The mixture was cooled to 20° C. and the precipitated product was filtered, washed With isopropanol and ether and dried in vacuo. (707 mg; 86%; M.P. 230°-240° C. (dec); LC-MS: 402 (MH+); anal. RP18-HPLC RT: 5.35 min.).

Workup

filtrationthe precipitated product was filtered
washwashed With isopropanol and ether
customdried in vacuo

Sources & evidence

ORD record: ord-af36d000608e465aa066040d03dfd18c
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE041065E1

Reaction notes

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