Phosphorus sulfide (P2S5) → HCID 54411746, compound

HRID 1602505Notes

Reaction equation

HRID 1602505 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:44]=[CH:45][CH:46]=2)[C:15]([NH:17][C:18]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:28]=[CH:27][C:19]=2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=O)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:48].C(=O)(O)[O-].[Na+]>COCCOC>[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:44]=[CH:45][CH:46]=2)[C:15]([NH:17][C:18]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)(=[O:36])=[O:35])[CH:28]=[CH:27][C:19]=2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[S:48])[S:8][CH:9]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 53953312HCID 53953312, compound

Product 1

HCID 54411746HCID 54411746, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 2-[3-[(4-tert-butyl-2-thiazolyl)methoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (176 mg, 0.26 mmol), diphosphorus pentasulfide (69 mg, 0.31 mmol), sodium bicarbonate (28 mg, 0.33 mmol) and 1,2-dimethoxyethane (5 ml) was stirred for 5 hours with heating under reflux, and insoluble matter was removed by filtration. The resulting filtrate was diluted with ethyl acetate, washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (eluent=hexane:ethyl acetate=3:1-2:1) to give ethyl 2-[3-[(4-tert-butyl-2-thiazolyl)methoxy]thiobenzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (143 mg, 0.20 mmol, 78%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. custominsoluble matter was removed by filtration
  4. additionThe resulting filtrate was diluted with ethyl acetate
  5. washwashed with water and brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThereafter, the resulting residue was purified by silica gel column chromatography (eluent=hexane:ethyl acetate=3:1-2:1)

Sources & evidence

ORD record
ord-139e2fb1b5f243e88c56184c01464b1a
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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