Water → HCID 9800720, compound

HRID 1290794Notes

Reaction equation

HRID 1290794 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[H-].[Na+].[CH3:16][O:17][C:18]1[C:23]2[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][C:29](SC)=[N:30][C:31]=3[C:22]=2[CH:21]=[CH:20][CH:19]=1.O>O1CCCC1>[CH3:16][O:17][C:18]1[C:23]2[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][C:29]([NH:6][C:5]4[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:30][C:31]=3[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 322853,4,5-TrimethoxyanilineHCID 18918773HCID 18918773, compound

Product 1

HCID 9800720HCID 9800720, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4,5-trimethoxyaniline (0.401 g) in tetrahydrofuran at room temperature under nitrogen was added sodium hydride (60% oil dispersion, 0.16 g) in portions over 2-3 minutes. The mixture was stirred for 15 minutes, and then 7-methoxy-2-methylthio-5,6-dihydrobenzo[h]quinazoline (0.258 g) was added, and the mixture was refluxed for 4 hours. The reaction mixture was poured into 300 ml of water, and the resulting yellow precipitate filtered off, washed with pentane, and dried under vacuum, giving 7-methoxy-2-(3,4,5-trimethoxyanilino)-5,6-dihydrobenzo[h]quinazoline (0.3042 g).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationthe resulting yellow precipitate filtered off
  3. washwashed with pentane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b8e7613b93484c60b38b33071a39df00
Source dataset
uspto-grants-1998_05
Patent number
US05753663

Reaction notes

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