N-bromobutanimide → 6-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 2104069Notes

Reaction equation

HRID 2104069 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:12]([Cl:21])[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH:6]=1)=[O:4].C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([Br:29])=[CH:19][CH:20]=2)=[C:12]([Cl:21])[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 865990177-Chloro-6-phenylamino-3H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 668983426-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl esterYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Chloro-6-phenylamino-3H-benzoimidazole-5-carboxylic acid methyl ester 7c (0.327 g, 1.08 mmol) is dissolved into DMF (16 mL) and NBS (0.193 g, 1.08 mmol) is added. After one hour, the reaction mixture is quenched by the addition of saturated aqueous NaHSO3. The reaction mixture is then partitioned between EtOAc/THF and water. The organic layer is washed with water and brine. The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure. The recovered solid is triturated with ether to give 0.225 g (54%) pure desired product. MS ESI (+) m/z 382, 384 (M+, Br pattern) detected.

Workup

  1. additionis added
  2. customthe reaction mixture is quenched by the addition of saturated aqueous NaHSO3
  3. customThe reaction mixture is then partitioned between EtOAc/THF and water
  4. washThe organic layer is washed with water and brine
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe recovered solid is triturated with ether

Sources & evidence

ORD record
ord-80f198491e2d49e0bd452c17c1a026c4
Source dataset
uspto-grants-2009_08
Patent number
US07576114B2

Reaction notes

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