Methyl N-(triethylammoniosulfonyl)carbamate → HCID 45255862, compound

HRID 1875857Notes

Reaction equation

HRID 1875857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][NH:24][C:25](=O)[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:22])[C:9]=2[S:31][CH3:32])=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[C:26]([C:25]1[O:22][C:21]([C:10]2[C:9]([S:31][CH3:32])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=2)=[N:23][N:24]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67320835HCID 67320835, compound

Product 1

HCID 45255862HCID 45255862, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(methylthio)-N′-pivaloyl-1H-pyrazole-3-carbohydrazide (9) (80 mg, 0.156 mmol) and Burgess reagent (111 mg, 0.468 mmol) in THF (5 mL) was irradiated in a microwave reactor (Biotage Initiator™) for 50 minutes at 155° C. The organic extract was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was subjected to flash column chromatography (Biotage SP1™) to obtain 38 mg (50%) of the title compound as a white solid.

Workup

  1. extractionThe organic extract
  2. dry with materialwas dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40148070ff854b079d7cb6cd149b16d0
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

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