Boron tribromide → HCID 178464675, compound

HRID 2273965Notes

Reaction equation

HRID 2273965 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]=[C:14]([NH:22][CH2:23][CH3:24])[N:15]2[CH2:19][CH:18]([CH2:20][CH3:21])[CH:17]=[N:16]2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]=[C:14]([NH:22][CH2:23][CH3:24])[N:15]2[CH2:19][CH:18]([CH2:20][CH3:21])[CH:17]=[N:16]2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178464674HCID 178464674, compound

Product 1

HCID 178464675HCID 178464675, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 25 mL DCM, 1.09 g 3-chloro-N-[ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-4-methoxy-benzenesulfonamide was dissolved, and 11.69 mL of a 1M solution of BBr3 in DCM was added. The mixture was stirred overnight at room temperature, extracted with 5% aqueous NaHCO3, dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM/EA 95:5) to yield 0.89 g (84%) of 3-Chloro-N-[ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-4-hydroxy-benzenesulfonamide as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 0.97 (t, J=7.52 Hz, 3H), 1.16 (t, J=7.22 Hz, 3H), 1.46-1.70 (m, 2H), 3.05-3.18 (m, 1H), 3.43-3.54 (m, 2H), 3.69 (dd, J=11.14, 7.52 Hz, 1H), 4.04-4.12 (m, 1H), 6.05 (br.s., 1H), 6.83 (br.s., 1H), 6.93 (d, J=1.50 Hz, 1H), 7.06 (d, J=8.43 Hz, 1H), 7.75 (dd, J=8.73, 2.11 Hz, 1H), 7.94 (d, J=2.11 Hz, 1H).

Workup

  1. extractionextracted with 5% aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (DCM/EA 95:5)

Sources & evidence

ORD record
ord-eec6953a335142179bd556bcb5ce411d
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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