N-bromobutanimide → HCID 89705488, compound

HRID 929062Notes

Reaction equation

HRID 929062 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].C1C(=O)N([Br:30])C(=O)C1>CN(C=O)C>[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:30])=[CH:18][C:17]=1[Cl:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89705463HCID 89705463, compound

Product 1

HCID 89705488HCID 89705488, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-fluoro-5-((2-chlorophenyl)amino)benzo[d][1,2,3]thiadiazole-6-carboxylate (1.82 g, 5.39 mmol) in DMF (10 mL) was added NBS (1.0 g, 5.65 mmol). After stirring for 4 h at ambient temperature, the reaction was quenched by saturated NH4Cl (aq.). The solution was extracted with ethyl acetate (30 mL×3). The combined organic extracts were washed with water (30 mL) and brine (30 mL) successively, dried over Na2SO4 and concentrated in vacuo to give the desired product (yellow solid, 2.02 g, 90.1% yield). 1H NMR (400 MHz, CDCl3): δ 8.84 (s, 1H), 8.60 (d, 1H), 7.59 (d, 1H), 7.29 (m, 1H), 6.77 (m, 1H), 4.04 (s, 3H).

Workup

  1. customthe reaction was quenched by saturated NH4Cl (aq.)
  2. extractionThe solution was extracted with ethyl acetate (30 mL×3)
  3. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL) successively
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05bf6c0f177140cfb8be276cceb3a449
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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