Dichloromethane → HCID 178434273, compound

HRID 1157404Notes

Reaction equation

HRID 1157404 reaction equation
F[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][NH2:12].C(Cl)Cl>C(O)CO>[CH3:2][C:3]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 99472-Fluoro-1-phenylethan-1-one

Product 1

HCID 178434273HCID 178434273, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A stirred solution of 2.0 g (14.48 mmol) of 2-fluoroacetophenone (32-1) in 10 mL of ethylene glycol under nitrogen was treated with 473 uL (15.06 mmol) of hydrazine. This solution was stirred for 2 hours at room temperature and then heated at 165° C. for 40 hours. The solution was cooled to room temperature, poured into CH2Cl2 (25 mL), and extracted with H2O (2×50 mL). The organic portions were combined, dried (MgSO4), filtered and conc. in vacuo. Purification of the crude material by recrystallization from hexanes/CHCl3 gave the desired product 32-2 as a tan solid. 1H NMR (DMSO-d6): δ 7.70 (d, 1H), 7.42 (m, 2H), 7.17 (dd, 1H), 2.60 (s, 3H).

Workup

  1. temperatureheated at 165° C. for 40 hours
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with H2O (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered and conc. in vacuo
  6. customPurification of the crude material
  7. customby recrystallization from hexanes/CHCl3

Sources & evidence

ORD record
ord-17f3a86f2564441cbb441e56ded50a84
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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