Water → HCID 57732200, compound

HRID 401786Notes

Reaction equation

HRID 401786 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=1)[CH2:24][C:25]1[O:29][N:28]=[C:27]([CH3:30])[CH:26]=1)=[N+]=[N-].O>C1COCC1.C(OCC)(=O)C>[Cl:37][C:33]1[CH:32]=[C:31]([CH:23]([NH2:20])[CH2:24][C:25]2[O:29][N:28]=[C:27]([CH3:30])[CH:26]=2)[CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57732014HCID 57732014, compound

Product 1

HCID 57732200HCID 57732200, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Triphenylphosphine (137 g, 0.522 mol, 1.19 eq) was added to a solution of 5-(2-azido-2-(3-chlorophenyl)ethyl)-3-methylisoxazole (Preparation 48, 115 g, 0.437 mol, 1 eq) in THF (1 L) under nitrogen atmosphere. The reaction mixture was stirred for 1 hr after which water (45 mL) was added and it was heated at 50° C. overnight. The reaction mixture was concentrated, the crude oil so obtained was dissolved in 1 L ethyl acetate and cooled to 0° C. It was extracted with 6M HCl (3×500 mL). The aqueous phase was saturated by sodium chloride and basified with 6M sodium hydroxide to pH-10 (2 L) and was extracted with ethyl acetate (2 L). Organics were washed by brine, dried and concentrated to yield a liquid, which solidifies upon refrigeration. The title compound was obtained as white solid (30 g, 0.127 mol, 29%).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude oil so obtained
  4. temperaturecooled to 0° C
  5. extractionIt was extracted with 6M HCl (3×500 mL)
  6. extractionwas extracted with ethyl acetate (2 L)
  7. washOrganics were washed by brine
  8. customdried
  9. concentrationconcentrated
  10. customto yield a liquid, which

Sources & evidence

ORD record
ord-ac5d409acdc1491aa379d26e95ec7134
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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