Lawesson's reagent → 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbothioamide

HRID 82717Notes

Reaction equation

HRID 82717 reaction equation
[NH2:1][C:2]1[C:3]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Br:17])[CH:11]=2)=O)=[N:4][S:5][N:6]=1.COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:27]2)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:7](=[S:27])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Br:17])[CH:11]=2)=[N:4][S:5][N:6]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 585582444-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carboxamide

Product 1

HCID 585583094-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbothioamideYield 55.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carboxamide (225 mg, 0.7 mmol) and 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (570 mg, 1.4 mmol) in toluene (6.8 mL) was stirred at 95° C. for 16 h. The reaction mixture was diluted with ethyl acetate (50 mL) and the insoluble salts were filtered. The filtrate was concentrated to a crude residue which was purified on silica gel to give the desired product (130 mg, 55%). LCMS for C9H7BrFN4S2 (M+H)+: m/z=332.8, 334.9.

Workup

  1. filtrationthe insoluble salts were filtered
  2. concentrationThe filtrate was concentrated to a crude residue which
  3. customwas purified on silica gel

Sources & evidence

ORD record
ord-bf4e5550eb00476595e5c06b5f2e6286
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

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