Benzylamine → N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide

HRID 526734Notes

Reaction equation

HRID 526734 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].[OH:29][CH2:30][C:31](=[O:34])[CH:32]=[CH2:33]>C(Cl)Cl.CCCCCCC.CC(C)([O-])C.[K+]>[CH2:1]([N:8]([CH2:33][CH2:32][C:31](=[O:34])[CH2:30][OH:29])[S:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[N+:16]([O-:18])=[O:17])(=[O:27])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 12369703Hydroxymethylvinyl ketone

Product 1

HCID 71152063N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamideYield 77%

Reagents, catalysts & solvents 3

HCID 23665647Potassium tert-butoxideCatalystHCID 6344DichloromethaneSolvent2×HCID 8900HeptaneSolvent

Procedure

To a solution of benzylamine (10.92 ml, 100 mmol) in DCM (150 ml) was added triethylamine (13.67 ml, 100 mmol) followed by a solution of 2-nitrobenzene-1-sulfonyl chloride (22.16 g, 100 mmol) in DCM (70 ml) at 5-10° C. with stirring. The mixture was stirred for 1 hour, stirring continued for 1 hour, washed with water, brine, most of DCM removed under reduced pressure. Ethyl acetate (150 ml) was added, another 25-30 ml distilled off under reduced pressure. To the resulting solution potassium tert-butoxide (0.561 g, 5.00 mmol) was added followed by 1-hydroxybut-3-en-2-one (9.47 g, 110 mmol) with stirring in one portion at 20-25° C. The mixture was stirred for 1 hour at 20-25° C., diluted with heptane (70 ml), washed with brine and 1N HCl (5 ml), organic phase was dried (MgSO4), evaporated to dryness under reduced pressure. The resulting oil was purified on a column with ethyl acetate-petroleum ether mixture as eluent. Fractions containing the wanted product were collected and evaporated to dryness under reduced pressure to give N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide (29.1 g, 77 mmol, 77% yield).

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. stirringstirring
  3. washwashed with water, brine, most of DCM
  4. customremoved under reduced pressure
  5. additionEthyl acetate (150 ml) was added
  6. distillationanother 25-30 ml distilled off under reduced pressure
  7. stirringwith stirring in one portion at 20-25° C
  8. stirringThe mixture was stirred for 1 hour at 20-25° C.
  9. washwashed with brine and 1N HCl (5 ml), organic phase
  10. dry with materialwas dried (MgSO4)
  11. customevaporated to dryness under reduced pressure
  12. customThe resulting oil was purified on a column with ethyl acetate-petroleum ether mixture as eluent
  13. additionFractions containing the wanted product
  14. customwere collected
  15. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6333af2d1d584caeba9447ad76f37f14
Source dataset
uspto-grants-2016_05
Patent number
US09346751B2

Reaction notes

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