Phosphorus oxychloride → HCID 86687456, compound

HRID 1473409Notes

Reaction equation

HRID 1473409 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)[S:7]([C:10]1[CH:19]=[C:18]2[C:13]([C:14](=O)[NH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].O=P(Cl)(Cl)[Cl:34]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:34][C:14]1[C:13]2[C:18](=[CH:19][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:3]=3[O:2][CH3:1])[C:21]3[S:22][CH:23]=[CH:24][N:25]=3)(=[O:9])=[O:8])=[CH:11][CH:12]=2)[N:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136409065HCID 136409065, compound

Product 1

HCID 86687456HCID 86687456, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2,4-dimethoxybenzyl)-4-oxo-N-(thiazol-2-yl)-3,4-dihydroquinazoline-7-sulfonamide (0.990 g, 2.159 mmol) was dissolved in toluene (10.80 ml) and POCl3 (0.403 ml, 4.32 mmol) was added. The reaction was stirred for 90 minutes at room temperature, then heated to 90° C. and stirred for four hours. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford a brown oily solid. The solid was triturated in heptane, stirred for 30 minutes, and filtered. The resulting material was vacuum dried to afford crude 4-chloro-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide as a free flowing tan solid. (ESI) 499.1 (M+Na)+.

Workup

  1. temperatureheated to 90° C.
  2. stirringstirred for four hours
  3. washwashed with saturated sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialthe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a brown oily solid
  9. customThe solid was triturated in heptane
  10. stirringstirred for 30 minutes
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-051e71b1bc544da49558a780e708ca6e
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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