Phosphorus sulfide (P2S5) → (2-Methoxy-5-morpholin-4-yl-phenylamino)-thioxo-acetic acid

HRID 1358235Notes

Reaction equation

HRID 1358235 reaction equation
C([O:3][C:4](=[O:22])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][C:9]=1[O:20][CH3:21])=O)C.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24]>C1(C)C(C)=CC=CC=1>[CH3:21][O:20][C:9]1[CH:10]=[CH:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:13][C:8]=1[NH:7][C:5](=[S:24])[C:4]([OH:3])=[O:22]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 21137088HCID 21137088, compound

Product 1

HCID 21919264(2-Methoxy-5-morpholin-4-yl-phenylamino)-thioxo-acetic acidYield 170.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 33.9g (110 mmol) N-(2-methoxy-5-morpholin-4-yl-phenyl)-oxalamic acid ethyl ester in 652 ml boiling xylene were added 8.80 g (40 mmol) phosphorus pentasulfide in small portions over a period of 30 minutes. The mixture was refluxed for 5 hours, cooled to room temperature and filtered. The solution was extracted 7 times with 100 ml 1N NaOH. The aqueous phase was washed twice with 100 ml toluene, filtered, and treated at 0-5° C. with concentrated hydrochloric acid until pH 1 was reached. Filtration of the precipitate yielded 20.2 g (62%) (2-methoxy-5-morpholin-4-yl-phenylamino)-thioxo-acetic acid as yellow crystals with mp.: 156-158° C., MS m/e (%): 297 (M+H+, 100).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. filtrationfiltered
  3. extractionThe solution was extracted 7 times with 100 ml 1N NaOH
  4. washThe aqueous phase was washed twice with 100 ml toluene
  5. filtrationfiltered
  6. additiontreated at 0-5° C. with concentrated hydrochloric acid until pH 1
  7. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-e91b19eea6ef43ba86fc6515299127c9
Source dataset
uspto-grants-2003_07
Patent number
US06596718B1

Reaction notes

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