2,2,2-Trifluoroethanol → HCID 11373783, compound

HRID 2113772Notes

Reaction equation

HRID 2113772 reaction equation
[C:1]1([C:7]2[C:8](=[O:25])[NH:9][C:10](=[O:24])[C:11]=2[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:57][C:58]([F:62])([F:61])[CH2:59]O>C1COCC1>[C:1]1([C:7]2[C:8](=[O:25])[N:9]([CH2:59][C:58]([F:62])([F:61])[F:57])[C:10](=[O:24])[C:11]=2[NH:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68408486HCID 68408486, compound

Product 1

HCID 11373783HCID 11373783, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-phenyl-4-{[4-(trifluoromethoxy)phenyl]amino}-1H-pyrrole-2,5-dione (0.63 mmol, 220 mg), diethyl azodicarboxylate (0.70 mmol, 121 mg) and triphenylphosphine (0.70 mmol, 182 mg) in dry THF (4 mL) was prepared in sealed reaction vessel. 2,2,2-Trifluoroethanol (0.70 mmol, 70 mg) was added. The mixture was first stirred at rt. for three days, then at 40° C. for two hours and finally at 100° C. for 30 min. in a microwave reactor. The reaction mixture was filtered and purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 7 mg (3%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.45 (s, br, 1H), 7.22-7.09 (m, 3H), 7.02-6.97 (m, 2H), 6.92-6.84 (m, 2H), 6.70-6.65 (m, 2H), 4.24 (q, J=8.6 Hz, 2H).

Workup

  1. customwas prepared in sealed reaction vessel
  2. waitat 40° C. for two hours
  3. waitfinally at 100° C. for 30 min. in a microwave reactor
  4. filtrationThe reaction mixture was filtered
  5. custompurified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record
ord-aabd652d006f49b1b05e08573533925b
Source dataset
uspto-grants-2008_10
Patent number
US07432288B2

Reaction notes

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