Dimethylformamide → HCID 67669427, compound

HRID 1384605Notes

Reaction equation

HRID 1384605 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=O)[NH:13][CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.S(Cl)([Cl:21])=O.CN(C=O)C.[OH:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[CH3:36])[NH2:32]>C(O)(C)C>[ClH:21].[OH:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[CH3:36])[NH:32][C:12]1[C:11]2[C:16](=[CH:17][C:8]([S:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:9][CH:10]=2)[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 178185-Amino-2-methylphenolHCID 24386Thionyl ChlorideHCID 135671183HCID 135671183, compound

Product 1

HCID 67669427HCID 67669427, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7-(4-pyridylthio)-3,4-dihydroquinazolin-4-one (100 mg, 0.4 mmol), thionyl chloride (20 ml) and DMF (0.1 ml) was heated at reflux for 1.5 hours. The volatiles were removed by evaporation and the residue azeotroped with toluene. A solution of 3-hydroxy-4-methylaniline (53 mg, 0.04 mmol) in isopropanol (10 ml) was added to the solid residue and the mixture was heated at reflux for 2 hours. The mixture was allowed to cool and the precipitated product collected by filtration, washed with isopropanol and dried to give 4-(3-hydroxy-4-methylanilino)-7-(4-pyridylthio)quinazoline hydrochloride(103 mg, 73%). 1H NMR Spectrum: (DMSOd6) 2.17(s, 3H); 7.05(dd, 1H); 7.17(d, 1H); 7.19(s, 1H); 7.64(d, 2H); 8.00(d, 1H); 8.20(s, 1H); 8.66(d, 2H); 8.92(s, 1H); 9.05(d, 1H) MS-ESI: 361 [MH]+

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customThe volatiles were removed by evaporation
  4. customthe residue azeotroped with toluene
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 2 hours
  7. temperatureto cool
  8. filtrationthe precipitated product collected by filtration
  9. washwashed with isopropanol
  10. customdried

Sources & evidence

ORD record
ord-5a189a0506cf47bab4b03efd751fed3f
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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