Water → HCID 21701856, compound

HRID 2224392Notes

Reaction equation

HRID 2224392 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.[N+:6]([C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7].C(N(CC)CC)C.O>O1CCOCC1>[N+:6]([C:9]1[CH:10]=[C:11]([S:15]([NH:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 75646Cyclopropanemethanamine

Product 1

HCID 21701856HCID 21701856, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of cyclopropylmethylamine (1.28 ml, 15 mmol) in dioxane (37 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (3.0 g, 14 mmol) and triethylamine (2.06 ml, 15 mmol). The light yellow suspension was stirred at room temperature for 4 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 3-nitro-N-cyclopropylmethyl-benzenesulfonamide (3.08 g, 89%) as an off-white solid. MS (ISP) 254.9 [(M−H)−]; m.p. 91° 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-d998f1292eeb41e397118544bf7e50bf
Source dataset
uspto-grants-2008_05
Patent number
US07378417B2

Reaction notes

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