Phosphorus sulfide (P2S5) → HCID 24760089, compound

HRID 1674665Notes

Reaction equation

HRID 1674665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:11]([S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)(=[O:28])=[O:27])[CH2:12][C:13]([N:15]([CH2:24][CH3:25])[CH2:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=1)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:40]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:11]([S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)(=[O:28])=[O:27])[CH2:12][C:13]([N:15]([CH2:24][CH3:25])[CH2:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=1)=[S:40]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 24760021HCID 24760021, compound

Product 1

HCID 24760089HCID 24760089, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[(2-chloro-5-dimethylamino-phenyl)-(3,4-dimethoxy-benzenesulfonyl)-amino]-N-ethyl-N-(6-methyl-pyrazin-2-ylmethyl)-acetamide (20 mg) in dry toluene (0.2 mL) was added in one portion phosphorus pentasulfide (10 mg). The reaction mixture was stirred at 80° C. under nitrogen for 3 h. After cooling to RT, the reaction mixture was concentrated under reduced pressure and the residue was purified by FC (EA/n-heptane: 8/2 to EA) to give 12 mg (57%) of the title compound as a foam.

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by FC (EA/n-heptane: 8/2 to EA)

Sources & evidence

ORD record
ord-d29f9ddb926c4c278f68616bd3e9d2cf
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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