Dimethylformamide → HCID 66986112, compound

HRID 1162461Notes

Reaction equation

HRID 1162461 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.CN(C=O)C.C(N(CC)C(C)C)(C)C.Br[CH2:34][C:35]([NH2:37])=[O:36]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[N:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:6]([CH2:34][C:35]([NH2:37])=[O:36])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 696322-BromoacetamideHCID 81531DiisopropylethylamineHCID 673877HCID 673877, compound

Product 1

HCID 66986112HCID 66986112, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a 250 mL round-bottomed flask was added N-(5-bromopyridin-2-yl)-4-methylbenzenesulfonamide (10.0 g, 31 mmol), DMF (60 mL), N,N-diisopropylethylamine (6.4 mL, 37 mmol) and 2-bromoacetamide (5.1 g, 37 mmol, Aldrich, St. Louis, Mo.). The mixture was stirred at 25° C. for 1 day. The mixture was poured into water (600 mL) and the solution was stirred for 1 h. The solution was filtered and the filtercake was washed with water and then dried in vacuo to afford the title compound as a white solid (10.2 g, 87%). MS (ESI, positive ion) m/z: 384 (M(79Br)+1).

Workup

  1. stirringthe solution was stirred for 1 h
  2. filtrationThe solution was filtered
  3. washthe filtercake was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b521e86cf4b5433bb8bea953617f07f5
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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