Triphenylphosphine → HCID 54752952, compound

HRID 447946Notes

Reaction equation

HRID 447946 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([OH:29])[CH3:28].N(C(OCC)=O)=NC(OCC)=O.[CH3:42][O:43][C:44]([C:46]1[S:47][C:48]([N:52]2[CH:56]=[N:55][C:54]([NH:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[N:53]2)=[CH:49][C:50]=1O)=[O:45]>C1COCC1.CN(C=O)C>[CH3:42][O:43][C:44]([C:46]1[S:47][C:48]([N:52]2[CH:56]=[N:55][C:54]([NH:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[N:53]2)=[CH:49][C:50]=1[O:29][CH:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[Cl:20])[CH3:28])=[O:45]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 260821-(2-Chlorophenyl)ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54752798HCID 54752798, compound

Product 1

HCID 54752952HCID 54752952, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triphenyl phosphine (124 mg, 0.47 mmol, 1.5 Eq.) was added to a stirred solution of 1-(2-Chloro-phenyl)-ethanol (74 mg, 0.47 mmol, 1.5 Eq.) in anhydrous THF (5 mL) at 0° C. under nitrogen. The reaction was stirred at this temperature for 30 minutes, then diethyl azodicarboxylate (75 μL, 0.47 mmol, 1.5 Eq.) was added dropwise and the reaction stirred at 0° C. for a further 1 hour. 3-Hydroxy-5-(3-phenylamino-[1,2,4]triazol-1-yl)-thiophene-2-carboxylic acid methyl ester (100 mg, 0.32 mmol, 1.0 Eq.) in anhydrous DMF (2 mL) was added and the reaction stirred for a further 1 hour at 0° C. then allowed to warm to ambient temperature overnight. The crude reaction mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with water (2×20 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/petroleum Ether) to give the sub-title compound as an off-white solid (88 mg, 0.19 mmol, 73%); 1H NMR (400 MHz, CDCl3) δ 1.74 (3H, d), 3.93 (3H, s), 5.84 (1H, q), 6.70 (1 h, br s), 6.74 (1H, s), 7.02 (1H, t), 7.21-7.40 (5H, m), 7.51 (1H, d), 7.63 (1H, d), 8.12 (1H, s).

Workup

  1. stirringthe reaction stirred at 0° C. for a further 1 hour
  2. stirringthe reaction stirred for a further 1 hour at 0° C.
  3. customThe crude reaction mixture
  4. customwas partitioned between EtOAc (50 mL) and water (50 mL)
  5. washThe organic phase was washed with water (2×20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/petroleum Ether)

Sources & evidence

ORD record
ord-bd3d5067924d480ba560ccc0a38605ea
Source dataset
uspto-grants-2013_07
Patent number
US08481578B2

Reaction notes

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