Hydrochloric Acid → HCID 11965693, compound

HRID 1894009Notes

Reaction equation

HRID 1894009 reaction equation
CO[C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH2:17].CC[N:21]([CH2:24]C)CC.[CH3:26][S:27]([NH:30]N)(=[O:29])=[O:28].[OH-:32].[Na+].Cl>C1COCC1.CCOC(C)=O>[C:10]([C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[C:13]([F:14])([F:15])[F:16])[NH:17][C:24](=[O:32])[N:21]([NH:30][S:27]([CH3:26])(=[O:29])=[O:28])[C:3]2=[O:18])(=[O:12])[CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 11965692HCID 11965692, compound

Product 1

HCID 11965693HCID 11965693, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-acetyl-2-amino-4-trifluoromethyl-benzoic acid methyl ester (10.2 g, 39.0 mmol) in THF (250 mL) was treated with (CCl3O)2CO (3.86 g, 12.9 mmol) and the mixture was stirred at r.t. for 15 min under nitrogen. To this solution was added Et3N (5.55 mL, 39.0 mmol) and the mixture was stirred for another 3 h at r.t. The mixture was then treated with CH3SO2NHNH2 (4.38 g, 39.0 mmol) and stirred for 1 h at r.t. Aqueous sodium hydroxide (1M, 78 mL, 78.0 mmol) was subsequently added and the solution was stirred for 18 h at r.t. The mixture was acidified with aqueous hydrochloric acid (4N) until pH=3-4, and then diluted with EtOAc. It was then washed once with water, and the organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated until the product precipitated. The suspension was then cooled to 0° C., and then filtered. The white solid was dried in vacuo to give N-(6-acetyl-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (12.1 g, 33.2 mmol, 85%), m.p. 258-265° C., ESI-MS: m/z 366 [M+H]+.

Workup

  1. stirringthe mixture was stirred for another 3 h at r.t
  2. stirringstirred for 1 h at r.t
  3. stirringthe solution was stirred for 18 h at r.t
  4. washIt was then washed once with water
  5. dry with materialthe organic phase was then dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated until the product
  8. customprecipitated
  9. temperatureThe suspension was then cooled to 0° C.
  10. filtrationfiltered
  11. customThe white solid was dried in vacuo

Sources & evidence

ORD record
ord-1ab9635dfa8f47ecb18f4da113d3fb86
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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