4-Methylmorpholine → HCID 67175502, compound

HRID 1256100Notes

Reaction equation

HRID 1256100 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.CN1CCOCC1.[CH3:19][O:20][CH2:21][CH2:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[S:32](Cl)(=[O:34])=[O:33]>CC#N>[OH:10][B:7]1[C:6]2[CH:11]=[C:2]([NH:1][S:32]([C:24]3[CH:25]=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:23]=3[CH2:22][CH2:21][O:20][CH3:19])(=[O:33])=[O:34])[CH:3]=[CH:4][C:5]=2[CH2:9][O:8]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655213HCID 86655213, compound

Product 1

HCID 67175502HCID 67175502, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (0.59 g, 3.9 mmol) and N-methylmorpholine (2.53 g, 25 mmol) in MeCN (70 mL) was added 2-(2-methoxyethyl)-4-nitrobenzene-1-sulfonyl chloride (1.4 g, 5 mmol) in MeCN (20 mL) at 0° C., then the solution was stirred at room temperature overnight. The mixture was concentrated in vacuo, and ethyl acetate and water was added to the residue. The organic layer was dried over Na2SO4 and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1 to 0:1) to give N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(2-methoxyethyl)-4-nitrobenzene sulfonamide (1 g, yield 50%).

Workup

  1. concentrationThe mixture was concentrated in vacuo, and ethyl acetate and water
  2. additionwas added to the residue
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1 to 0:1)

Sources & evidence

ORD record
ord-afac37dbeffb43269a354d4cf36fd873
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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