3-Nitrobenzenesulfonyl chloride → HCID 62522906, compound

HRID 2224400Notes

Reaction equation

HRID 2224400 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH2:14][C:15]1([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH:14][C:15]2([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 663071-AminocyclopentanemethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 62522906HCID 62522906, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-nitro-benzenesulfonyl chloride (0.89 g, 4 mmol) and (1-amino-cyclopentyl)-methanol (0.46 g, 4 mmol) in dichloromethane (4 mL)/sat. sodium bicarbonate solution (4 mL) was stirred at 20° C. for 20 h. The mixture was diluted with dichloromethane (20 mL). The layers were separated and the organic layer was washed with water, dried (Na2SO4) and evaporated in vacuo. The solid residue was dissolved in ethanol (20 mL) and hydrogenated in the presence of 5% palladium-charcoal (0.2 g) to give the title compound (0.64 g, 59%). Off-white solid. MS (ISP) 271.4 [(M+H)+]; mp 130-132° C.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. dissolutionThe solid residue was dissolved in ethanol (20 mL) and hydrogenated in the presence of 5% palladium-charcoal (0.2 g)

Sources & evidence

ORD record
ord-a032a08aa548404da49e65adcb643859
Source dataset
uspto-grants-2008_05
Patent number
US07378417B2

Reaction notes

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