Sodium Hydroxide → Chloroform methanol ammonia

HRID 725811Notes

Reaction equation

HRID 725811 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH:10]1[CH:11]=[CH:12][C:13]2[N:20]=[CH:19][NH:18][C:16](=[O:17])[C:14]=2[CH:15]=1.N.[CH3:22]O.[CH:24]([Cl:27])([Cl:26])[Cl:25].C[C:29]([N:31](C)C)=[O:30]>>[CH3:29][O:30][C:10]1[C:15]([S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[C:14]2[C:13](=[CH:12][CH:11]=1)[N:20]=[C:19]([CH3:22])[NH:18][C:16]2=[O:17].[NH3:31].[CH3:16][OH:17].[CH:24]([Cl:27])([Cl:26])[Cl:25]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 21866414Chloroform methanol ammoniaHCID 1354087534(1H)-QuinazolinoneHCID 178418431pyridine-4-thiol

Product 2

HCID 21866414Chloroform methanol ammoniaHCID 135524511HCID 135524511, compound

Conditions

Temperature
135 °C

Procedure

To 78 mg (0.7 mmol) of 4-Mercaptopyridine was added 34 mg (0.5 mmol) of solid NaOH in 1 ml of dry DNA. To the resulting solution, 134 mg (0.5 mmol) of quinazolinone (16) dissolved in 2 ml dry DMA was added. The mixture was kept under N2, and a finely ground catalyst mixture containing 44 mg CuBr and 22 mg Cu2O was added The mixture was stirred magnetically and heated to 135° C., until the reaction was complete as judged by TLC (anh. NH3 /MeOH/CHCl3 ; 0.5: 4.5: 9.5). The solvent was removed under high vacuum through a cryogenic trap cooled to -78° C. The desired product was isolated by flash chromatography (anh. NH3 /MeOH/CHCl3 ; 0.5: 4.5: 9.5) on silica, yielding 130 mg (89%) of (17) as a white powder. M.P. 248°-249° C. (dec.). IR (KBr) 3358, 3073, 2933, 1682, 1634, 1574, 1475, 1462, 1318, 1277, 1059, 835, 710 cm-1 ; 1H NMR (CDCl3) δ 2.36 (s, 3H), 3.84 (s, 3H), 6.90 (d, 2H, J=5.1 Hz), 7.48 (d, 1H, J=9.1 Hz), 7.79 (d, 1H, J=9.1 Hz), 8.28 (d, 2H, J=5.1 Hz), 10 86 (s, 1H). Anal. Calcd. For C15H13N3O2S: C, 60.18; H, 4.38; N, 14.04; S, 10.71. Found: C, 60.28; H, 4.43; N, 14.07; S, 10.63. HRMS Calcd. For C15H13N3O2S: 299.0730. Found: 299.0718.

Workup

  1. additionwas added
  2. additionwas added The mixture
  3. customThe solvent was removed under high vacuum through a cryogenic trap
  4. temperaturecooled to -78° C

Sources & evidence

ORD record
ord-85c4ca22f46942d6a323f9485ad063ad
Source dataset
uspto-grants-1998_01
Patent number
US05707992

Reaction notes

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