HCID 18669510, compound → HCID 12044419, compound

HRID 1058989Notes

Reaction equation

HRID 1058989 reaction equation
C([N:8](CC1C=CC=CC=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:28])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])C1C=CC=CC=1>C(O)(=O)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:19]2[C:19](=[O:20])[CH:18]=[C:15]([CH3:14])[O:28][C:18]=2[C:15]2[CH:14]=[CH:13][C:12]([S:9]([NH2:8])(=[O:10])=[O:11])=[CH:17][CH:16]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 18669510HCID 18669510, compound

Product 1

HCID 12044419HCID 12044419, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of N,N-dibenzyl-4-[2-(4-chlorophenoxy)acetyl]benzenesulfonamide (11.7 g, 23 mmoles) in acetic acid(105 ml), polyphosphoric acid (75 g) was added and the resulting solution was heated at 140° C. for 5 hours. After cooling, the reaction mixture was poured into ice-water, extracted with ethyl acetate (3×150 ml), and the organic solution was dried (Na2SO4). The solvent was removed under reduced pressure and the resulting oil was solved in H2SO4 (33 ml). The mixture was stirred at room temperature for 15 minutes, and poured into ice-water. The solid was filtered off and purified by column chromatography silica gel and ethyl acetate/methylene chloride/acetic acid (78:10:1) as eluent. 4-[3-(4-chlorophenoxy)-6-methyl-4-oxo-4H-pyran-2-yl]benzenesulfonamide (0.28 g) was obtained. m.p. 221° C. (Compound 57 in Table 4).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×150 ml)
  3. dry with materialthe organic solution was dried (Na2SO4)
  4. customThe solvent was removed under reduced pressure
  5. additionpoured into ice-water
  6. filtrationThe solid was filtered off
  7. custompurified by column chromatography silica gel and ethyl acetate/methylene chloride/acetic acid (78:10:1) as eluent

Sources & evidence

ORD record
ord-56c2d04d4a6542df8f0ef0fd2c63bbcc
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

Loading…