Phosphorus sulfide (P2S5) → HCID 22093487, compound

HRID 457995Notes

Reaction equation

HRID 457995 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH2:15]([O:17][C:18](=[O:44])[CH2:19][O:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28](=O)[NH:29][CH2:30][C:31]1[S:32][C:33]2[C:39]([F:40])=[CH:38][C:37]([F:41])=[C:36]([F:42])[C:34]=2[N:35]=1)[CH3:16]>N1C=CC=CC=1.O.C(OCC)(=O)C>[CH2:15]([O:17][C:18](=[O:44])[CH2:19][O:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28](=[S:2])[NH:29][CH2:30][C:31]1[S:32][C:33]2[C:39]([F:40])=[CH:38][C:37]([F:41])=[C:36]([F:42])[C:34]=2[N:35]=1)[CH3:16]

Participants

6

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 22093486HCID 22093486, compound

Product 1

HCID 22093487HCID 22093487, compoundYield 68.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

In a flame dried flask under a nitrogen atmosphere, a suspension of phosphorus pentasulfide (2.9 g, 6.4 mmol) in pyridine (26 mL) was treated with {5-Fluoro-2[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)carbamoyl]-phenoxy}-acetic acid ethyl ester (Example 54, 5.7 g, 13 mmol) and heated to 115° C. for 4 h. After cooling to room temperature, the mixture was diluted with water and ethyl acetate. The organic layer was washed successively with 2 N HCl (2×) and saturated NaCl, dried over MgSO4, and concentrated. The resulting brown oil was chromatographed by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min) to give {5-fluoro-2-[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiocarbamoyl]-phenoxy}-acetic acid ethyl ester (2.0 g, 34%): 1H NMR (DMSO-d6 300 MHz) δ 10.98 (br s, 1 H), 7.79 (br t, J=6.0 Hz, 2 H), 7.06 (br d, J=11.1 Hz, 1 H), 6.90 (br t, J=9 Hz, 1 H), 5.38 (br s, 2 H), 4.89 (s, 2 H), 4.12 (q, J=7.2 Hz, 2 H), 1.16 (t, J=7.1 3 H).

Workup

  1. customIn a flame dried flask under a nitrogen atmosphere
  2. temperatureAfter cooling to room temperature
  3. washThe organic layer was washed successively with 2 N HCl (2×) and saturated NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting brown oil was chromatographed by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min)

Sources & evidence

ORD record
ord-f2a3baea15cd49a59e9110cbc7110d5d
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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