Dichloromethane → Ethanesulfonamide, 2-(diethylamino)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-

HRID 2266666Notes

Reaction equation

HRID 2266666 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH:19]=[CH2:20])(=[O:18])=[O:17])=[CH:11][CH:10]=2)[O:3]1.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23].C(OCC)(=O)C.ClCCl>CO>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:21])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH2:19][CH2:20][N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])(=[O:18])=[O:17])=[CH:13][CH:14]=2)[O:5]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 58886388Ethenesulfonic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]amide

Product 1

HCID 58886021Ethanesulfonamide, 2-(diethylamino)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-Yield 56.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ethenesulfonic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide (0.500 g, 1.6 mmol) in methanol (5 mL) was added diethylamine (0.707 g, 4.0 mmol) in methanol (5 mL), and the reaction was stirred at room temperature and monitored by TLC (1:1 Ethyl acetate:hexanes). After 2 hr the reaction was concentrated in vacuum and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate was then washed with 50% brine (1×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Crude product was purified using a 10 g prepacked silica gel column, eluting with 1:1 ethyl acetate:dichloromethane to provide 2-diethylamino-ethanesulfonic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide as a white solid (0.346 g, 0.90 mmol, 56%). 1H NMR (CDCl3, 300 MHz) δ 7.78 (d, J=6.65, 2H) 7.15 (d, J=6.66, 2H), 3.20 (m, 2H), 3.0 (m, 2H), 2.55 (q, J=7.15, 7.16 4H), 1.34 (s, 12H), 1.05 (t, J=7.19, 6H).

Workup

  1. concentrationAfter 2 hr the reaction was concentrated in vacuum
  2. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. washThe ethyl acetate was then washed with 50% brine (1×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customCrude product was purified
  8. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-1f4dda0f93f84d709081b013a5bdf782
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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