Methyl triflate → Methyl 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbimidothioate

HRID 386821Notes

Reaction equation

HRID 386821 reaction equation
[NH2:1][C:2]1[C:3]([C:7](=[S:17])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Br:16])[CH:10]=2)=[N:4][S:5][N:6]=1.F[C:19](F)(F)S(OC)(=O)=O.C(N(CC)C(C)C)(C)C>ClCCl>[NH2:1][C:2]1[C:3]([C:7]([S:17][CH3:19])=[N:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Br:16])[CH:10]=2)=[N:4][S:5][N:6]=1

Participants

5

Reactant 3

HCID 9526Methyl triflateHCID 81531DiisopropylethylamineHCID 585583094-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbothioamide

Product 1

HCID 58558200Methyl 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbimidothioateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbothioamide (130 mg, 0.4 mmol) in dichloromethane (5.2 mL) was treated with methyl trifluoromethanesulfonate (64 μL, 0.6 mmol) followed by N,N-diisopropylethylamine (102 μL, 0.6 mmol) and stirred for 1 h. The reaction mixture was diluted with dichloromethane (100 mL), washed with water (50 mL) and brine (50 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (133 mg, 98%). LCMS for C10H9BrFN4S2 (M+H)+: m/z=346.8, 348.8.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52909698cb10419ea5372442ce491ed0
Source dataset
uspto-grants-2013_02
Patent number
US08372870B2

Reaction notes

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