Ammonia → HCID 16639421, compound

HRID 2233267Notes

Reaction equation

HRID 2233267 reaction equation
[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1.N>C(O)C.O.C(O)(=O)C.[Fe]>[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

7

Reactant 2

HCID 222AmmoniaHCID 16638417HCID 16638417, compound

Product 1

HCID 16639421HCID 16639421, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Iron powder (325 mesh, 1.35 g, 52 mmol) was added portionwise to a stirred solution of 4-(methylthio)-7-nitroquinazoline (1.44 g, 6.52 mmol) in ethanol (130 ml), water (65 ml) and acetic acid (1.15 ml) at reflux over 1.5 hours. The mixture was cooled to 50° C., and a solution of ammonia (28%, 5 ml) was added. The precipitate was collected by suction filtration, washed with warm ethanol and the solvent was evaporated in vacuo. Purification by flash chromatography on by silica gel, eluting with 5% methanol in dichloromethane, yielded 4-(methylthio)-7-aminoquinazoline (1.17 g, 94% yield):

Workup

  1. temperatureat reflux over 1.5 hours
  2. filtrationThe precipitate was collected by suction filtration
  3. washwashed with warm ethanol
  4. customthe solvent was evaporated in vacuo
  5. customPurification by flash chromatography on by silica gel
  6. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-4eea222780e741838ee79ff1e5bfabb9
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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