Ethanol → HCID 14373423, compound

HRID 1649703Notes

Reaction equation

HRID 1649703 reaction equation
[F:1][CH:2]([F:22])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13](=[O:16])[S:14][CH3:15])=[C:5]([NH2:17])[C:4]=1[C:18](=[O:21])SC.C(O)C.[OH-:26].[Na+]>C(OCC)(=O)C>[NH2:17][C:5]1[C:4]([C:18]([OH:21])=[O:26])=[C:3]([CH:2]([F:1])[F:22])[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]=1[C:13]([S:14][CH3:15])=[O:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 14373417HCID 14373417, compound

Product 1

HCID 14373423HCID 14373423, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 40.8 g (0.113 mol) of product of Example 191, 400 ml of ethanol and 4.5 g (0.113 mol) of 10% aqueous sodium hydroxide was stirred at 25° C. for 5 days. Another 2 g (0.05 mol) of sodium hydroxide was added and stirring continued for 24 hours. The reaction mixture was then diluted with ethyl acetate and washed with three 500 ml portions of 5% HCl, dried (CaSO4), filtered and concentrated to 31.4 g (84%) of product as a yellow solid; mp 219° C. (dec).

Workup

  1. washwashed with three 500 ml portions of 5% HCl
  2. dry with materialdried (CaSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to 31.4 g (84%) of product as a yellow solid

Sources & evidence

ORD record
ord-e1934d96ee0f49039d5e50dd4e6f5cd8
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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