Potassium Carbonate → HCID 15508758, compound

HRID 1275521Notes

Reaction equation

HRID 1275521 reaction equation
[C:1]([C:5](=[O:37])[CH:6](Cl)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:14])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][C:40]=1[NH:49][S:50]([CH3:53])(=[O:52])=[O:51].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:35][C:34]1[CH:33]=[CH:32][C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:14])=[CH:11][C:10]=1[NH:9][C:7]([CH:6]([O:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][C:40]=1[NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[C:5](=[O:37])[C:1]([CH3:4])([CH3:3])[CH3:2])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15476485Benzoic acid, 4-chloro-3-[(2-chloro-4,4-dimethyl-1,3-dioxopentyl)amino]-, hexadecyl esterHCID 15508757Benzoic acid, 4-hydroxy-3-[(methylsulfonyl)amino]-, methyl ester

Product 1

HCID 15508758HCID 15508758, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 8.35 g (15 mmol) of 2, 3.68 g (15 mmol) of methyl 4-hydroxy-3-(methanesulfonamido)-benzoate 3 and 6.22 g (45 mmol) of potassium carbonate in 180 mL of acetone was heated at reflux overnight. Thin layer chromatographic analysis indicated reaction was complete. The solvent was removed under vacuum to near dryness, and the residue was treated with a mixture of ethyl acetate and water. The organic liquid phase was washed with dilute hydrochloric acid and then with brine, and then concentrated under vacuum to an oil. The crude product was purified by column chromatography on silica gel using an elution solvent of 30 volume percent ethyl acetate in ligroin. There was thus obtained 7 g (61% yield ) of coupler Y-1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customreaction
  4. customThe solvent was removed under vacuum
  5. additionthe residue was treated with a mixture of ethyl acetate and water
  6. washThe organic liquid phase was washed with dilute hydrochloric acid
  7. concentrationwith brine, and then concentrated under vacuum to an oil
  8. customThe crude product was purified by column chromatography on silica gel using an elution solvent of 30 volume percent ethyl acetate in ligroin

Sources & evidence

ORD record
ord-e74b7b2eab0349e9bbb774726391f074
Source dataset
uspto-grants-2000_12
Patent number
US06162598

Reaction notes

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