HCID 10026206, compound → HCID 10091253, compound

HRID 1090184Notes

Reaction equation

HRID 1090184 reaction equation
COC([C:5]1[C:14]2[C:8]([CH:9]=[CH:10][C:11]([CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[C:7]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:6]=1)=O>P(=O)(O)(O)O>[CH:15]([C:11]1[CH:10]=[CH:9][C:8]2[C:14](=[CH:13][CH:12]=1)[CH:5]=[CH:6][C:7]=2[CH2:18][CH2:19][CH2:20][CH2:21][NH:22][S:23]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:24])([CH3:17])[CH3:16]

Participants

3

Reactant 1

HCID 10026206HCID 10026206, compound

Product 1

HCID 10091253HCID 10091253, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

A solution of 6-Isopropyl-3-[4-(benzenesulfonylamino)butyl]-azulene-1-carboxylic acid methyl ester (1.53 g) in 100% phosphoric acid (13 ml) was stirred at 120° C. for 20 min. The reaction mixture was poured on ice-water, and extracted with ethyl acetate. The ethyl acetate extracts were washed with water and dried over MgSO4. Removal of the solvent and the purification by silica gel columnchromatography (ethyl acetate-n-hexane, 1:3) afforded the title compound (1.23 g 94%) as a violet crystal 75°~76° C.

Workup

  1. additionThe reaction mixture was poured on ice-water
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts were washed with water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent
  6. customthe purification by silica gel columnchromatography (ethyl acetate-n-hexane, 1:3)

Sources & evidence

ORD record
ord-9c144278d2b84f5a94850c129e17c772
Source dataset
uspto-grants-1992_01
Patent number
US05081152

Reaction notes

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