Boron tribromide → HCID 178464655, compound

HRID 2273971Notes

Reaction equation

HRID 2273971 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:6][N:5]([C:7]([NH:20][CH2:21][CH3:22])=[N:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)(=[O:11])=[O:10])[N:4]=[CH:3]1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:23])[CH2:6][N:5]([C:7]([NH:20][CH2:21][CH3:22])=[N:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)(=[O:11])=[O:10])[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 178464656HCID 178464656, compound

Product 1

HCID 178464655HCID 178464655, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 mL DCM, 2.32 g N-[(4,4-Dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-3-methoxy-benzenesulfonamide was dissolved, and 13.7 mL of a 1M solution of BBr3 in DCM was added. The mixture was stirred over weekend at room temperature. A 5% aqueous NaHCO3 solution was added to quench the mixture that contained a sticky precipitate; after quenching, this was dissolved by gently heating the mixture. The organic layer was separated and the aqueous layer was extracted once more with DCM. The combined organic layers were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM/MeOH 99:1→98:2) to yield 1.24 g (56%) N-[(4,4-Dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-3-hydroxybenzenesulfonamide as of a beige powder. 1HNMR (400 MHz, CDCl3) δ 1.09 (t, J=7 Hz, 3H), 1.14 (s, 6H), 3.40-3.50 (m, 2H), 3.58 (br.s., 2H), 6.72 (s, 1H), 6.79 (br.s., 1H), 6.97-7.03 (m, 1H), 7.25-7.34 (m, 2H), 7.46 (br d, J=8 Hz, 1H), 7.66 (br s, 1H).

Workup

  1. customto quench the mixture
  2. customafter quenching
  3. dissolutionthis was dissolved
  4. temperatureby gently heating the mixture
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted once more with DCM
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography (DCM/MeOH 99:1→98:2)

Sources & evidence

ORD record
ord-d8283dd111114a85a19247e5035a8bc6
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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