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

HRID 2210020Notes

Reaction equation

HRID 2210020 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-18747f63f067490b8780599c90632356
Source dataset
uspto-grants-1995_10
Patent number
US05457105

Reaction notes

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