Thionyl Chloride → HCID 18326463, compound

HRID 1250608Notes

Reaction equation

HRID 1250608 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:18][CH2:19][CH2:20]O)[N:6]=1)[CH:2]=[CH2:3].S(Cl)([Cl:24])=O>ClCCl>[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:18][CH2:19][CH2:20][Cl:24])[N:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 183265262-[[6-Nitro-4-(2-propen-1-ylamino)-2-quinazolinyl]amino]ethanol

Product 1

HCID 18326463HCID 18326463, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 mg (0.173 mmol) of 4-allylamino-2-(2-hydroxyethylamino)-6-nitroquinazoline in dichloromethane was added 1.63 g (13.7 mmol) of thionyl chloride, and then the resulting mixture was stirred at room temperature for 4 hours. After the mixture was subjected to heating under reflux for further one hour, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel chromatography to give 25 mg (yield: 46.8%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for further one hour
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-e13c626be95e4fdbbc345a7b36c27c8e
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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