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Phosphorus trichloride → HCID 11648458, compound

HRID 1039371
Notes
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Reaction equation

HRID 1039371 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:30])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH3:17])[N:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](=[O:28])(=[O:27])[NH:25][CH3:26])[C:9]2=[O:29])=[O:5])[CH3:2].C(O[C:34](=O)[C:35]1C(C)=CC(NC(=O)C)=C(C(O)=O)[C:36]=1C)C.NC1C=CC=CC=1S(NC)(=O)=O.P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH:2]1([CH2:1][O:3][C:4]([C:6]2[C:7]([CH3:30])=[C:8]3[C:13](=[CH:14][C:15]=2[CH3:16])[N:12]=[C:11]([CH3:17])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24](=[O:28])(=[O:27])[NH:25][CH3:26])[C:9]3=[O:29])=[O:5])[CH2:36][CH2:35][CH2:34]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24387Phosphorus trichlorideHCID 11328402-amino-N-methylbenzene-1-sulfonamideHCID 11185063HCID 11185063, compoundHCID 668153082,5,7-Trimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid ethyl ester

Product 1

HCID 11648458HCID 11648458, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Preparation of 2,5,7-Trimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid ethyl ester: A heterogeneous mixture of 4-Acetylamino-2,6-dimethyl-isophthalic acid 1-ethyl ester (5.39 g, 1.95 mmol), 2-amino-N-methyl-benzenesulfonamide (3.63 g, 1.95 mmol), and phosphorus trichloride (8.5 mL, 9.7 mmol) in toluene (220 mL) was heated at 140° C. (oil bath temperature) for 3.5 h. The reaction mixture was allowed to cool to room temperature and then evaporated in vacuo. Sufficient ethyl acetate was added to dissolve the residue and the solution was washed with saturated aqueous sodium hydrogen carbonate then brine, dried (Na2SO4) and evaporated in vacuo. Trituration of the residue with dichloromethane gave a white solid, which was removed by filtration. Evaporation of the filtrate solution followed by trituration with ethyl acetate provided a second crop of white solid. The evaporation-trituration procedure was repeated to give two further crops of white solid. The combined white solids were washed with ether and dried in vacuo to provide the title compound.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated in vacuo
  3. additionSufficient ethyl acetate was added
  4. dissolutionto dissolve the residue
  5. washthe solution was washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialbrine, dried (Na2SO4)
  7. customevaporated in vacuo
  8. customTrituration of the residue with dichloromethane gave a white solid, which
  9. customwas removed by filtration
  10. customEvaporation of the filtrate solution
  11. customprovided a second crop of white solid
  12. customThe evaporation-trituration procedure
  13. customto give two further crops of white solid
  14. washThe combined white solids were washed with ether
  15. customdried in vacuo

Sources & evidence

ORD record
ord-f0f90da6239249e0ba81801029ddd472
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552015B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes