Water → HCID 21248631, compound

HRID 1194632Notes

Reaction equation

HRID 1194632 reaction equation
NC1C=CC(O[C:7]2[C:8]([Cl:25])=[CH:9][C:10]([F:24])=[C:11]([C:13]34[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]3[C:17](=[O:23])[NH:16][C:14]4=[O:15])[CH:12]=2)=CC=1.S(=O)(=O)(O)O.N([O-])=[O:34].[Na+].[C:37]1(C)[C:38](C)=[CH:39][CH:40]=[CH:41][CH:42]=1.[OH2:45]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:25][C:8]1[C:7]([O:45][C:41]2[CH:42]=[CH:37][C:38]([OH:34])=[CH:39][CH:40]=2)=[CH:12][C:11]([C:13]23[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[C:17](=[O:23])[NH:16][C:14]3=[O:15])=[C:10]([F:24])[CH:9]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 7237O-XyleneHCID 21248633HCID 21248633, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21248631HCID 21248631, compound

Reagents, catalysts & solvents 1

HCID 24463Copper sulfate pentahydrateCatalyst

Conditions

Temperature
20 °C

Procedure

While maintaining a temperature of 20°-25° C., 1.7 g (0.0040 mole) of 1-[5-(4-aminophenoxy)-4-chloro-2-fluorophenyl]-3,4,5,6-tetrahydrophthalimide was added to 4.0 mL of stirred, concentrated sulfuric acid. To this was added a solution of 0.40 g (0.0055 mole) of sodium nitrite dissolved in 6 mL of water, while continuing to maintain a temperature of about 20° C. After complete addition, the mixture was stirred at 20° C. for 30 minutes. This mixture was added through a glass tube to the bottom of a stirred, refluxing mixture of 30.0 g (0.120 mole) of copper (II) sulfate pentahydrate, 90 mL of water and 30 mL of xylene. After complete addition the mixture was refluxed for one hour. The mixure was cooled, and the organic phase was extracted with an aqueous, sodium hydroxide solution (6.0 g of sodium hydroxide dissolved in 250 mL of water). The basic extract was acidified with concentrated hydrochloric acid and was extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to yield 0.6 g of 1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy)phenyl]-2,3,4,5-tetrahydrophthalimide as an oil.

Workup

  1. additionwas added to 4.0 mL
  2. additionAfter complete addition
  3. stirringthe mixture was stirred at 20° C. for 30 minutes
  4. additionThis mixture was added through a glass tube to the bottom of a stirred
  5. temperaturerefluxing
  6. additionAfter complete addition the mixture
  7. temperaturewas refluxed for one hour
  8. temperatureThe mixure was cooled
  9. extractionthe organic phase was extracted with an aqueous, sodium hydroxide solution (6.0 g of sodium hydroxide dissolved in 250 mL of water)
  10. extractionThe basic extract
  11. extractionwas extracted with diethyl ether
  12. extractionThe organic extract
  13. dry with materialwas dried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-23a8e48ef16c462780a476ac73e38ead
Source dataset
uspto-grants-1989_03
Patent number
US04816065

Reaction notes

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