Water → HCID 69286973, compound

HRID 2224399Notes

Reaction equation

HRID 2224399 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[N+:8]([C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].C(N(CC)CC)C.O>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)(=[O:18])=[O:19])([CH2:5][OH:6])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 15312-Amino-2-methyl-1,3-propanediolHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 69286973HCID 69286973, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-amino-2-methyl-1,3-propanediol (1.04 ml, 9.93 mmol) in dioxane (25 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (2.0 g, 9.02 mmol) and triethylamine (1.38 ml, 9.93 mmol). The light yellow suspension was stirred at room temperature for 6 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) to yield N-(2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-3-nitro-benzenesulfonamide (0.65 g, 25%) as a white solid. MS (ISP) 289.1 [(M−H)−]; mp 116° C.

Workup

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3ee0c795131f4a6e9e1f825a70c50985
Source dataset
uspto-grants-2008_05
Patent number
US07378417B2

Reaction notes

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