(4-Chlorophenyl)(2-sulfanylidene-1,3-benzoxazol-3(2H)-yl)methanone → HCID 13342156, compound

HRID 483176Notes

Reaction equation

HRID 483176 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][C:8]1[C:9](=[O:19])[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([OH:18])=[CH:13][CH:12]=2)[C:4]([OH:6])=[O:5].[Cl:20][C:21]1[CH:38]=[CH:37][C:24]([C:25](N2C3C=CC=CC=3OC2=S)=[O:26])=[CH:23][CH:22]=1>CN1CCCC1=O>[Cl:20][C:21]1[CH:38]=[CH:37][C:24]([C:25]([NH:2][CH:3]([CH2:7][C:8]2[C:9](=[O:19])[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([OH:18])=[CH:13][CH:12]=3)[C:4]([OH:6])=[O:5])=[O:26])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 19003889(4-Chlorophenyl)(2-sulfanylidene-1,3-benzoxazol-3(2H)-yl)methanoneHCID 67820135HCID 67820135, compound

Product 1

HCID 13342156HCID 13342156, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2 Grams of 2-amino-3-(6-hydroxy-2-quinolon-3-yl)propionic acid hydrochloride was suspended in 50 ml of 1-methyl-2-pyrrolidone, then 2.2 g of 3-(4-chlorobenzoyl)benzoxazoline-2-thione was added thereto and stirred at a room temperature for 3 days. The reaction mixture was poured in ice-water and the crystals precipitated were collected by filtration. The crystals were dissolved in 1N-sodium hydroxide aqueous solution, and acidified with 10%-hydrochloric acid, then the crystals precipitated were collected by filtration. The crystals were dried and washed with chloroform. Recrystallized from methanol-water to obtain 1.5 g of 2-(4-chlorobenzoylamino)-3-(6-hydroxy-2-quinolon-3-yl)propionic acid in the form of light yellowish powdery product.

Workup

  1. customthe crystals precipitated
  2. filtrationwere collected by filtration
  3. dissolutionThe crystals were dissolved in 1N-sodium hydroxide aqueous solution
  4. customthe crystals precipitated
  5. filtrationwere collected by filtration
  6. customThe crystals were dried
  7. washwashed with chloroform
  8. customRecrystallized from methanol-water

Sources & evidence

ORD record
ord-5639364cf35e42139cac772fcafb9aee
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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