Sulfuric Acid → HCID 22647966, compound

HRID 394218Notes

Reaction equation

HRID 394218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](O)([CH3:20])[CH3:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:30])[N:13]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29].[Br:31][CH2:32][C:33]#[N:34].S(=O)(=O)(O)[OH:36]>C(O)(=O)C>[Br:31][CH2:32][C:33]([NH:34][C:18]([C:16]1[CH:15]=[C:14]2[C:9]([CH2:10][NH:11][C:12](=[O:30])[N:13]2[C:22]2[C:23]([Cl:29])=[CH:24][CH:25]=[CH:26][C:27]=2[Cl:28])=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:17]=1)([CH3:19])[CH3:20])=[O:36]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11534BromoacetonitrileHCID 22648052HCID 22648052, compound

Product 1

HCID 22647966HCID 22647966, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred suspension of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(1-hydroxy-1-methylethyl)-3,4-dihydroquinazolin-2(1H)-one (460 mg) in acetic acid (0.4 mL) was added bromoacetonitrile (0.1 mL). To this mixture was added concentrated sulfuric acid (0.2 mL) and the resulting solution was allowed to stir overnight. The reaction was quenched by dropwise addition of the mixture to a rapidly stirred mixture of 2N aqueous NaOH and CH2Cl2. Transferred to a separatory funnel, diluted with water and extracted 3× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was purified by flash column chromatography on silica gel eluting with 2:1 hexanes/acetone giving 2-bromo-N-{1-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methylethyl}acetamide.

Workup

  1. customThe reaction was quenched by dropwise addition of the mixture to a rapidly stirred mixture of 2N aqueous NaOH and CH2Cl2
  2. additionTransferred to a separatory funnel, diluted with water
  3. extractionextracted 3× with CH2Cl2
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography on silica gel eluting with 2:1 hexanes/acetone

Sources & evidence

ORD record
ord-fceb79adbfa54d25be96cd0ed17cabf0
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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