Carbon Tetrachloride → HCID 18924988, compound

HRID 1288892Notes

Reaction equation

HRID 1288892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:12][CH2:13][CH2:14][O:15][CH3:16])[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.[C:42]([C:44]1[CH:45]=[C:46]([CH:48]=[CH:49][CH:50]=1)[NH2:47])#[CH:43]>ClCCCl.C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:12][CH2:13][CH2:14][O:15][CH3:16])[N:8]=[CH:7][N:6]=[C:5]2[NH:47][C:46]1[CH:48]=[CH:49][CH:50]=[C:44]([C:42]#[CH:43])[CH:45]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 136008347HCID 136008347, compound

Product 1

HCID 18924988HCID 18924988, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3776IsopropanolSolvent

Procedure

6-Chloro-7-(2-methoxyethylsulfanyl)-quinazolin-4-one (200 mg, 0.739 mmol), triphenylphosphine (427 mg, 1.63 mmol) and 0.7 mL of carbon tetrachloride were refluxed in 4 ml of 1,2-dichloroethane for 4 hours, concentrated in vacuo to a residue, diluted with 4 mL of isopropyl alcohol and 3-ethynylaniline (129 mg, 1.104 mmol) and refluxed for 16 hours. The hot reaction mixture was filtered to isolate crude product which was column chromatographed on silica gel eluted with 5% methanol in chloroform. Fractions containing the pure product were concentrated in vacuo to afford the title product as a solid; 23 mg (8.4%); mp 230°-232° C.

Workup

  1. concentrationconcentrated in vacuo to a residue
  2. temperaturerefluxed for 16 hours
  3. filtrationThe hot reaction mixture was filtered
  4. customto isolate crude product which
  5. customchromatographed on silica gel
  6. washeluted with 5% methanol in chloroform
  7. additionFractions containing the pure product
  8. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-6e63212a4e434ab0835ab8b9e428f1d1
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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