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

HRID 1627530Notes

Reaction equation

HRID 1627530 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 588860212-(Diethylamino)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamideYield 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-426536fc0f8f4009bd5df1f54a6b569b
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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