Trifluoroacetic acid → HCID 58625002, compound

HRID 271631Notes

Reaction equation

HRID 271631 reaction equation
[CH2:1]([N:4]1[C:8]([C:10]2[CH:14]=[C:13]([CH3:15])[S:12][C:11]=2[CH3:16])(O)[CH:7]([C:17]2[CH:21]=[C:20]([CH3:22])[S:19][C:18]=2[CH3:23])[O:6][C:5]1=[O:24])[CH:2]=[CH2:3].C(O)(C(F)(F)F)=O>>[CH2:1]([N:4]1[C:8]([C:10]2[CH:14]=[C:13]([CH3:15])[S:12][C:11]=2[CH3:16])=[C:7]([C:17]2[CH:21]=[C:20]([CH3:22])[S:19][C:18]=2[CH3:23])[O:6][C:5]1=[O:24])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58625014HCID 58625014, compound

Product 1

HCID 58625002HCID 58625002, compound

Procedure

A solution of 0.9 g (2.5 mmol) of 1,3-oxazolane-2-one 7 in 25 ml (0.325 mol) of CF3COOH was stirred at ˜25° C. for 3-3.5 hours. The solvent was evaporated under vacuum and the residue was crystallized from ethanol. The yield was 0.63 g of oxazole 8 (73%), Tmelt=103-104° C. The results found (%): C, 62.43; H, 5.62; S, 18.78. C18H19NO2S2. The results calculated (%): C, 62.58; H, 5.54; S, 18.56. 1H NMR spectrum (DMSO-d6, δ, ppm): 1.99 (s, 3H, CH3); 2.12 (s, 3H, CH3); 2.27 (s, 3H, CH3); 2.32 (s, 3H, CH3); 4.03 (d, 2H, CH2, J=6 Hz); 4.93 (d, 1H, CH, J=17 Hz); 5.09 (d, 1H, CH, J=10 Hz); 5.73 (m, 1H, CH); 6.37 (s, 1H, CH); 6.74 (s, 1H, CH).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was crystallized from ethanol
  3. customThe yield was 0.63 g of oxazole 8 (73%), Tmelt=103-104° C

Sources & evidence

ORD record
ord-c07a6f64de1e40828389b76263d2407f
Source dataset
uspto-grants-2008_11
Patent number
US07452950B2

Reaction notes

Loading…