Water → HCID 54358825, compound

HRID 1816760Notes

Reaction equation

HRID 1816760 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][C@H:25]([CH3:27])[O:24][C@H:23]([CH3:28])[CH2:22]3)=[CH:17][CH:16]=2)=O)=[CH:6][CH:5]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:32].O.[OH-].[Na+]>C(COC)OC>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:32][C:14]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][C@H:25]([CH3:27])[O:24][C@H:23]([CH3:28])[CH2:22]4)=[CH:17][CH:16]=3)=[N:13][N:12]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 53959969HCID 53959969, compound

Product 1

HCID 54358825HCID 54358825, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-[N′-[4-(cis-2,6-dimethylmorpholin-4-yl)benzoyl]hydrazinocarbonyl]benzoic acid methyl ester (100 mg) in dimethoxyethane (3 ml) was added phosphorus pentasulfide (82 mg). The mixture was refluxed for 5 hours. After cooling to ambient temperature, the reaction mixture was poured into cold water and the mixture was adjusted to pH 11 with 1N-sodium hydroxide aqueous solution. The resulting precipitates were filtered, washed with water and dried to give 4-[5-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl][1,3,4]thiadiazol-2-yl]benzoic acid methyl ester (97.4 mg).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-11229a73eb4e44299598752703714929
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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