Triethylamine → N-benzyl-N-(3-hydroxy-4,4-dimethoxybutyl)-2-nitrobenzenesulfonamide

HRID 526732Notes

Reaction equation

HRID 526732 reaction equation
[CH2:1]([NH:8]/[CH:9]=[CH:10]/[C:11](=[O:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(N(CC)CC)C.[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37])([O-:29])=[O:28]>CC(O)C.O>[CH2:1]([N:8]([CH2:9][CH2:10][CH:11]([OH:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[S:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N+:27]([O-:29])=[O:28])(=[O:37])=[O:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 4311764Sodium borohydrideHCID 89315947(E)-4-(benzylamino)-1,1-dimethoxybut-3-en-2-one

Product 1

HCID 89315569N-benzyl-N-(3-hydroxy-4,4-dimethoxybutyl)-2-nitrobenzenesulfonamideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-4-(benzylamino)-1,1-dimethoxybut-3-en-2-one (1.176 g, 5 mmol) in a mixture of 2-Propanol (12.5 ml) and Water (1.200 ml) was added sodium borohydride (0.757 g, 20.00 mmol) in portions, the mixture was stirred for 7 hours. Quenched with 5N HCl to pH 7 (approx 2.5 ml), pH adjusted to 8-9 with 5N NaOH, diluted with MTBE (25 ml) and brine (15 ml). Organic phase was separated, triethylamine (0.767 ml, 5.50 mmol) was added with ice-cooling followed by 2-nitrobenzene-1-sulfonyl chloride (1.108 g, 5.00 mmol). The mixture was left at 0-5° C. (fridge) overnight. Washed with water, dried, evaporated to dryness, the residue applied on a column, eluted with petroleum ether-ethyl acetate mixture 1:1, fractions collected to give N-benzyl-N-(3-hydroxy-4,4-dimethoxybutyl)-2-nitrobenzenesulfonamide (1.9 g, 4.48 mmol, 90% yield), yellow oil.

Workup

  1. customQuenched with 5N HCl to pH 7 (approx 2.5 ml)
  2. additiondiluted with MTBE (25 ml) and brine (15 ml)
  3. customOrganic phase was separated
  4. temperaturecooling
  5. waitThe mixture was left at 0-5° C. (fridge) overnight
  6. washWashed with water
  7. customdried
  8. customevaporated to dryness
  9. washeluted with petroleum ether-ethyl acetate mixture 1:1, fractions
  10. customcollected

Sources & evidence

ORD record
ord-dee53f03fcc14567aec571c133ac2af4
Source dataset
uspto-grants-2016_05
Patent number
US09346751B2

Reaction notes

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