Carbon Tetrachloride → HCID 18925015, compound

HRID 1869099Notes

Reaction equation

HRID 1869099 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:12]=[CH:11][NH:10][C:9]2=O)[CH2:2][CH2:3][CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:42].[C:46]([C:48]1[CH:49]=[C:50]([CH:52]=[CH:53][CH:54]=1)[NH2:51])#[CH:47]>C(O)(C)C>[ClH:42].[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[NH:51][C:50]1[CH:52]=[CH:53][CH:54]=[C:48]([C:46]#[CH:47])[CH:49]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 136161589HCID 136161589, compound

Product 1

HCID 18925015HCID 18925015, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6,7-Dibutoxyquinazolin-4-one (105 mg, 0.362 mmol), triphenylphosphine (208 mg, 0.796 mmol) and 5 mL of carbon tetrachloride were refluxed for 16 hours and the reaction mixture was concentrated in vacuo to a residue which was diluted with 3 mL of isopropyl alcohol and 3-ethynylaniline (47 mg, 0.398 mmol) and refluxed for 3 hours. The cooled reaction mixture was filtered to afford solid (6,7-dibutoxy-quinazolin-4-yl)-(3-ethynyl-phenyl)-amine hydrochloride which was washed with 10 mL of isopropyl alcohol and dried in vacuo at 70° C., 92 mg (60%); mp 247°-248° C.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo to a residue which
  2. temperaturerefluxed for 3 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-f8e758b638f24ea193ddeedc80880a8b
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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