Phosphorus oxychloride → HCID 86662380, compound

HRID 1908953Notes

Reaction equation

HRID 1908953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]1[N:15]=[N:16][C:17]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[C:8]1[NH:7][C:6]2=O.O=P(Cl)(Cl)[Cl:30]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:30][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]2[N:15]=[N:16][C:17]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[C:8]2[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486776HCID 178486776, compound

Product 1

HCID 86662380HCID 86662380, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 7,8-dimethoxy-3-(phenylsulfonyl)-[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one (262 mg, 0.68 mmol) and tetrabutylammonium chloride (189 mg, 0.68 mmol) in POCl3 (10 mL) was heated at 120° C. for 30 min and then cooled to room temperature. After removal of POCl3 in vacuo, the residue was purified by column chromatography on silica gel eluting with 30% ethyl acetate in hexane to yield 5-chloro-7,8-dimethoxy-3-(phenylsulfonyl)-[1,2,3]triazolo[1,5-a]quinazoline (162 mg, 59%). 1H NMR (CDCl3, 600 MHz) δ 8.28-8.26 (m, 2H), 8.04 (s, 1H), 7.61 (s, 1H), 7.60-7.58 (m, 1H); 7.56-7.54 (m, 2H), 4.18 (s, 3H), 4.10 (s, 3H); MS (ES+) m/z 405.0 (M+H)+

Workup

  1. temperaturecooled to room temperature
  2. customAfter removal of POCl3 in vacuo
  3. customthe residue was purified by column chromatography on silica gel eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-62ff18bcb3f6401b8ba857c6c54b27ea
Source dataset
uspto-grants-2013_12
Patent number
US08598342B2

Reaction notes

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