Methanethiol → 6-chloro-7-methylthioquinazolin-4(3H)-one

HRID 34626

反応式

HRID 34626 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]=[CH:7][NH:6][C:5]2=[O:13].[H-].[Na+].[CH3:16][SH:17]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:17][CH3:16])[N:8]=[CH:7][NH:6][C:5]2=[O:13]

参加物

5

反応物 3

HCID 878MethanethiolHCID 24758Sodium hydrideHCID 1354602346,7-Dichloroquinazolin-4(3H)-one

生成物 1

HCID 1357451546-chloro-7-methylthioquinazolin-4(3H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
120 °C

実験手順

Under a nitrogen atmosphere in a flame dried flask equipped with a magnetic stirrer and a reflux condenser, a mixture of 1.00 g (0.00465 mol) of 6,7-dichloroquinazolin-4(3H)-one and 18 ml of dimethylformamide was treated at room temperature with 0.56 g (0.012 mol) of 50% sodium hydride in mineral oil. Foaming began immediately and most of the solids dissolved. When the foaming had subsided, 1.8 ml (0.0176 mol) of 47% methyl mercaptan in dimethyl formamide was added to the stirred mixture. The mixture was heated at 120° C. for six hours. When the reaction mixture was again at room temperature, a small amount of insoluble matter was filtered, and was rinsed with a few ml of dimethylformamide. The filtrate was washed three times with 10 ml portions of hexane. The filtrate was then poured into 300 ml of ice and water. By the addition of 2N hydrochloric acid, the aqueous solution was adjusted to pH 2. There formed a fine colorless precipitate which was filtered, washed with water, air dried and pressed on a clay plate to furnish the title compound: yield 0.97 g (92%); m.p. 292°-295° C. (dec.); mass spectrum m/e 226 (parent peak and molecular ion with expected isotope pattern), 193 (-33) among others; 1H-NMR(DMSO-d6) 2.6 ppm (singlet, 3H, SCH3), 7.45 (singlet, 1H, aromatic H), 8.0 (singlet, 1H, aromatic H), 8.15 (singlet, 1H, N=CH--N).

後処理

  1. customUnder a nitrogen atmosphere in a flame dried flask
  2. customequipped with a magnetic stirrer and a reflux condenser
  3. dissolutiondissolved
  4. customwas again at room temperature
  5. filtrationa small amount of insoluble matter was filtered
  6. washThe filtrate was washed three times with 10 ml portions of hexane
  7. additionThe filtrate was then poured into 300 ml of ice and water
  8. additionBy the addition of 2N hydrochloric acid
  9. customThere formed a fine colorless precipitate which
  10. filtrationwas filtered
  11. washwashed with water, air
  12. customdried

出典と根拠

ORDレコード
ord-5aacbb45634049febd018c40bf2f8592
出典データセット
uspto-grants-1988_08
特許番号
US04762838

関連ノート

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