Sodium Chloride → N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine

HRID 2103615Notes

Reaction equation

HRID 2103615 reaction equation
CO[CH:3]([N:6]([CH3:8])[CH3:7])OC.[Br:9][C:10]1[S:14][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:12][CH:11]=1.[Cl-].[Na+]>CN(C=O)C>[CH3:7][N:6]([CH:3]=[N:18][S:15]([C:13]1[S:14][C:10]([Br:9])=[CH:11][CH:12]=1)(=[O:17])=[O:16])[CH3:8]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 78373Dimethylformamide dimethyl acetalHCID 12413045-Bromo-2-thiophenesulfonamide

Product 1

HCID 54319951N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidineYield 114.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add dimethoxymethyl-dimethyl-amine (1.05 mL, 7.66 mmol) to a solution-of 5-bromo-thiophene-2-sulfonic acid amide (1.8 g, 7.43 mmol) in DMF (3 mL) at r.t. for 16 h. Pour reaction mixture into saturated sodium chloride, extract with ethylacetate. Wash combined organic layers with water, dry over sodium sulfate and remove solvent to obtain 2.52 g product. MS (m/e): 297.0/299.0 (M+H).

Workup

  1. additionPour
  2. extractionextract with ethylacetate
  3. washWash
  4. dry with materialdry over sodium sulfate
  5. customremove solvent

Sources & evidence

ORD record
ord-c03efdef1d594c498a5dc8be1f6972cb
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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