Water → HCID 58188162, compound

HRID 1845140Notes

Reaction equation

HRID 1845140 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][C:7]=1[S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 58188252HCID 58188252, compound

Product 1

HCID 58188162HCID 58188162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with 4-(1-azidomethyl)-1-methyl-2-(methylsulfonyl)benzene (5.0 g, 22.17 mmol), THF (40 mL), triphenylphosphine (6.4 g, 24.3 mmol) and water (1.6 mL, 34.2 mmol) at 0° C., and the reaction mixture was stirred at room temperature over night. The solvents were removed and the residue was dissolved in MTBE and 20% HCl in dioxane was added dropwise at 0° C. and the resulting salt was collected and washed with EtOAc. The salt was then neutralized with 6N aq. NaOH and extracted with CH2Cl2. The organic layers were concentrated under reduced pressure to get the title compound as a very thick oil. 1H NMR (400 MHz, CDCl3): 7.98 (s, 1H), 7.50 (d, 1H, J=8.0 Hz), 7.32 (d, 1H, J=8.0 Hz), 3.93 (s, 2H), 3.08 (s, 3H), 2.69 (s, 3H).

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in MTBE
  3. addition20% HCl in dioxane was added dropwise at 0° C.
  4. customthe resulting salt was collected
  5. washwashed with EtOAc
  6. extractionextracted with CH2Cl2
  7. concentrationThe organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-60e6e567b66b4c7bbebaaac5dc589bfb
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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