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

HRID 2210020노트

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HRID 2210020 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 199631224-(3'-Methylanilino)-6-methylthiomethylquinazoline수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-18747f63f067490b8780599c90632356
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05457105

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