HCID 19850150, compound → HCID 19850156, compound

HRID 1608011Notes

Reaction equation

HRID 1608011 reaction equation
C(O[CH:4](OCC)[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH:12]=[CH:11][C:10]=1[O:24][CH3:25])=[O:7])C>S(=O)(=O)(O)O>[CH3:25][O:24][C:10]1[CH:11]=[CH:12][C:13]([CH2:15][CH2:16][NH:17][C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])=[C:14]2[C:9]=1[NH:8][C:6](=[O:7])[CH:5]=[CH:4]2

Participants

3

Reactant 1

HCID 19850150HCID 19850150, compound

Product 1

HCID 19850156HCID 19850156, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The product of (a) (17.0 g, 42 mmoles) was added cautiously to concentrated sulphuric acid (50 ml) with stirring. When the addition was complete the dark solution was heated at 100° for 45 min then cooled and poured into ice-water. The suspension was extracted with ethyl acetate, and the extracts washed with sodium bicarbonate solution and water, dried and evaporated to give the sub-title compound as a pale yellow solid (11.0 g) mp 181°-184°. A sample recrystallised from ethanol-cyclohexane formed colourless needles mp 185°-186°.

Workup

  1. additionWhen the addition
  2. temperaturewas heated at 100° for 45 min
  3. temperaturethen cooled
  4. extractionThe suspension was extracted with ethyl acetate
  5. washthe extracts washed with sodium bicarbonate solution and water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-f13419e04f824a07a2ed8e09e683dd70
Source dataset
uspto-grants-1989_09
Patent number
US04868306

Reaction notes

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