Water → HCID 9862550, compound

HRID 2258434Notes

Reaction equation

HRID 2258434 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:22][CH2:23][CH3:24])=[C:16]([N+:19]([O-])=O)[CH:17]=2)[N:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](=S)=[S:26].C(N(CC)CC)C.O>C(O)C>[CH2:1]([NH:8][C:9]1[C:18]2[CH:17]=[C:16]3[NH:19][C:25](=[S:26])[N:22]([CH2:23][CH3:24])[C:15]3=[CH:14][C:13]=2[N:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 22921950HCID 22921950, compound

Product 1

HCID 9862550HCID 9862550, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Amino-4-benzylamino-7-ethylaminoquinazoline (4.5 g, 15.4 mmol) obtained, according to the procedures in Example 1, from 4-benzylamino-7-ethylamino-6-nitroquinazoline obtained in Reference Example 3 was suspended in ethanol (300 ml). To the suspension were added carbon disulfide (25 ml) and triethylamine (9.3 ml, 66.4 mmol), followed by heating under reflux for 6.5 hours. Water was added to the reaction mixture and the resulting crystals were filtered and recrystallized from a mixed solvent of dimethylformamide and ethanol to give the title compound (3.54 g, 60.6%).

Workup

  1. customobtained in Reference Example 3
  2. temperatureby heating
  3. temperatureunder reflux for 6.5 hours
  4. filtrationthe resulting crystals were filtered
  5. customrecrystallized from a mixed solvent of dimethylformamide and ethanol

Sources & evidence

ORD record
ord-a928fd8b4a11416bbbf7f58473318cc2
Source dataset
uspto-grants-1997_08
Patent number
US05661147

Reaction notes

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