Hydrochloric Acid → HCID 58473620, compound

HRID 870118Notes

Reaction equation

HRID 870118 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([Br:18])[CH:12]=2)C(=O)C2=CC=CC=C12.O.NN.Cl>C(O)C>[Br:17][C:15]1[CH:16]=[C:11]([CH:12]=[C:13]([Br:18])[CH:14]=1)[O:10][CH2:9][CH2:8][CH2:7][CH2:6][NH2:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 59848141HCID 59848141, compound

Product 1

HCID 58473620HCID 58473620, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(4′-Phthalimidobutoxy)3,5-dibromobenzene (1.0 g, 2.20 mmol) was dissolved in ethanol (45 mL) for 5 minutes under nitrogen. Hydrazine monohydrate (610 mg, 12.1 mmol) was added and the reaction was refluxed at 80° C. for 2 hours. To the reaction aqueous 1M HCl (17.7 mL, 17.7 mmol) was added and refluxed at 105° C. for another 2 hours. The aqueous layer was extracted with dichloromethane (2×150 mL). The organic layers were combined, washed with saturated NaHCO3 (3×), water, and brine, then dried over MgSO4, and filtered. Removal of solvent yielded a yellow oil (560 mg, 78%).

Workup

  1. temperaturerefluxed at 105° C. for another 2 hours
  2. extractionThe aqueous layer was extracted with dichloromethane (2×150 mL)
  3. washwashed with saturated NaHCO3 (3×), water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-8219429150f643b0b48213d64ac967a7
Source dataset
uspto-grants-2015_03
Patent number
US08969509B2

Reaction notes

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