Chlorosuccinimide → HCID 56944561, compound

HRID 2367987Notes

Reaction equation

HRID 2367987 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[B:10]([OH:17])[O:11][CH:12]([CH2:13][N+:14]([O-:16])=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2].C1C(=O)N([Cl:25])C(=O)C1>CN(C=O)C>[Cl:25][C:7]1[C:8]2[CH:12]([CH2:13][N+:14]([O-:16])=[O:15])[O:11][B:10]([OH:17])[C:9]=2[C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57451841HCID 57451841, compound

Product 1

HCID 56944561HCID 56944561, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 7-ethoxy-3-(nitromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (42 g, 0.18 mol) in DMF (200 mL) at 80° C. was added a solution of NCS (11.8 g, 0.18 mol) in DMF (50 mL) in 30 min. The reaction was quenched with an aqueous solution of LiCl solution (500 mL) and the resulting mixture was extracted by EtOAc (3×250 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the compound as white solid. (39.7 g, contaminated with 18% C6-C1 regioisomer). The mixture was then re-crystallized from Ether/PE (1/5) to give the pure compound (28 g, yield 46.3%). 1H NMR (400 MHz, DMSO-d6) δ 9.32 (s, 1H), 7.50-7.48 (d, 1H), 6.98-6.96 (d, 1H), 5.77-5.74 (d, 1H), 5.35-5.31 (d, 1H), 4.73-4.67 (m, 1H), 4.12-4.07 (m, 2H), 1.34-1.28 (t, 3H).

Workup

  1. customThe reaction was quenched with an aqueous solution of LiCl solution (500 mL)
  2. extractionthe resulting mixture was extracted by EtOAc (3×250 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-019edb3a822b4a49bc462b4ee5763895
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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