Triethylamine → 4-(3'-Methylanilino)-6-methylthiomethylquinazoline

HRID 2210020ノート

反応式

HRID 2210020 の反応式
[CH3:1][S-:2].[Na+].Br[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[NH:16][C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:5][S:2][CH3:1])[CH:7]=2)[N:12]=[CH:11][N:10]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 4378561Sodium methanethiolateHCID 224784026-Bromomethyl-4-(3-methylanilino)quinazoline

生成物 1

HCID 199631224-(3'-Methylanilino)-6-methylthiomethylquinazoline収率 38%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium methanethiolate (0.141 g) was added to a stirred mixture of 6-bromomethyl-4-(3'-methylanilino)quinazoline (0.6 g), triethylamine (0.203 g) and DMF (2 ml). The mixture was stirred at ambient temperature for 4 hours. The mixture was evaporated and the residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained an oil which was triturated under a mixture of hexane and diethyl ether to give 4-(3'-methylanilino)-6-methylthiomethylquinazoline (0.205 g), m.p. 134°-136° C. NMR Spectrum: (CD3SOCD3) 2.01 (s, 3H), 2.34 (s, 3H), 3.88 (s, 2H), 6.97 (d, 1H), 7.28 (t, 1H), 7.6 (m, 2H), 7.75 (d, 1H), 7.83 (m, 1H), 8.45 (d, 1H), 8.58 (s, 1H), 9.8 (broad s, 1H); Elemental Analysis: Found C, 69.7; H, 5.8; N, 14.21 C17H17N3S. 0.1C6H14 requires C, 69.5; H, 6.1; N, 13.8%.

後処理

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography
  3. temperatureusing increasingly polar mixtures of methylene chloride and ethyl acetate as eluent
  4. customThere was thus obtained an oil which
  5. customwas triturated under a mixture of hexane and diethyl ether

出典と根拠

ORDレコード
ord-18747f63f067490b8780599c90632356
出典データセット
uspto-grants-1995_10
特許番号
US05457105

反応ノート

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