Hydrochloric Acid → HCID 67275537, compound

HRID 1698492Notes

Reaction equation

HRID 1698492 reaction equation
[N:1]([CH:4]([C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][CH2:17][CH3:18])=[CH:11][CH:10]=1)[C:5]([CH3:8])([CH3:7])[CH3:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.Cl>C1COCC1.CO>[CH3:6][C:5]([CH3:7])([CH3:8])[CH:4]([C:9]1[CH:10]=[CH:11][C:12]([S:15][CH2:16][CH2:17][CH3:18])=[CH:13][CH:14]=1)[NH2:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 86635956HCID 86635956, compound

Product 1

HCID 67275537HCID 67275537, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1-(1-azido-2,2-dimethylpropyl)-4-(propylthio)benzene (282 mg, 1.07 mmol) in THF (8 ml) were added triphenylphosphine (842 mg, 3.21 mmol) and water (2 ml). The mixture was heated at 50° C. for 18 hours then allowed to cool to room temperature. Methanol (10 ml) was added and the mixture was passed through an SCX cartridge, which had been pre-treated with HCl in MeOH, eluting first with several column lengths of methanol to remove the triphenylphosphine oxide, then with 2M solution of ammonia in methanol to elute the product. The appropriate fractions were evaporated to give the title product as a pale yellow oil (231 mg). 1H NMR 3 (CDCl3) 7.27-7.19 (4H, m), 3.67 (1H, s), 2.89 (2H, t, J=7.3 Hz), 1.72-1.62 (2H, m), 1.02 (3H, t, J=7.3 Hz), 0.89 (9H, s).

Workup

  1. temperatureto cool to room temperature
  2. washeluting first with several column lengths of methanol
  3. customto remove the triphenylphosphine oxide
  4. washwith 2M solution of ammonia in methanol to elute the product
  5. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-39217b6954fb4302b7ae865c72e11692
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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