Dichloromethane → HCID 135689138, compound

HRID 463546Notes

Reaction equation

HRID 463546 reaction equation
C(Cl)Cl.[SH:4][C:5]1[NH:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.Br[CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18]([OH:20])=[O:19]>C(N(CC)CC)C>[O:15]=[C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([S:4][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([OH:20])=[O:19])[NH:14]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 97919Bromo(phenyl)acetic acidHCID 178518761HCID 178518761, compound

Product 1

HCID 135689138HCID 135689138, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution of 8.9 g (0.05M) of 2-mercapto-4(3H)-quinazolinone, α-bromophenylacetic acid and triethylamine is heated to gentle reflux for 48 hours. A small amount of insoluble material is filtered off and then the solvent is removed. The oily residue is dissolved in water and insoluble material filtered off. The aqueous filtrate is acidified with a dilute HCl solution and the gummy solid is extracted with methylene chloride. The methylene chloride solution is dried over anhydrous magnesium sulfate. After the solvent is removed the residual solid is dissolved in 500 ml hot acetonitrile, and upon cooling the solid is filtered. The filtrate, upon standing, gives 5.0 g (31% yield) of product which has a melting point of 184°-5° C. dec.

Workup

  1. temperatureto gentle reflux for 48 hours
  2. filtrationA small amount of insoluble material is filtered off
  3. customthe solvent is removed
  4. dissolutionThe oily residue is dissolved in water
  5. filtrationinsoluble material filtered off
  6. extractionthe gummy solid is extracted with methylene chloride
  7. dry with materialThe methylene chloride solution is dried over anhydrous magnesium sulfate
  8. customAfter the solvent is removed the residual solid
  9. dissolutionis dissolved in 500 ml hot acetonitrile
  10. temperatureupon cooling the solid
  11. filtrationis filtered

Sources & evidence

ORD record
ord-8c8f56d31c004ce595dc837eac6461f3
Source dataset
uspto-grants-1985_05
Patent number
US04520196

Reaction notes

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