4-Nitrobenzenesulfonyl chloride → HCID 178429795, compound

HRID 246107Notes

Reaction equation

HRID 246107 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][C@H:15]([CH3:18])[CH2:16]O.C(OCC)(=O)C.C(N(CC)C(C)C)(C)C>C(#N)C.N1C=CC=CC=1.O>[CH3:16][CH:15]1[CH2:18][N@:14]1[S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

8

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 80308(R)-(-)-2-Amino-1-propanolHCID 81531Diisopropylethylamine

Product 1

HCID 178429795HCID 178429795, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

4-Nitrobenzene-1-sulfonyl chloride (6.9 g, 31 mmol) was dissolved in acetonitrile (8 ml) and stirred in an ice bath. A solution of (R)-2-aminopropan-1-ol (1 g, 13.3 mmol) in pyridine (5 ml) was added slowly and the reaction was stirred for 2 h. Ethyl acetate (25 ml) and water (10 ml) were added and the reaction was stirred for 10 min. The layers were separated and the organic layer was washed with 1M citric acid solution twice and with water once. The organic layer was cooled to 10° C. and 7 ml of water was added followed by dropwise addition of N,N-diisopropylethylamine (3.7 ml, 21.3 mmol). After stirring for 1 h the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed twice with 1M citric acid solution and twice with water. Isopropanol (70 ml) was then added and the solvents were evaporated slowly leaving mostly isopropanol. (R)-2-Methyl-1-(4-nitro-benzenesulfonyl)-aziridine 2.2 g (69%) was obtained after crystallization from isopropanol. 1H NMR (300 MHz, CDCl3) δ: 8.40 (d, J=9.1 Hz, 2H), 8.16 (d, J=9.1 Hz, 2H), 2.92-3.04 (m, 1H), 2.74 (d, J=7.2 Hz, 1H), 2.13 (d, J=4.5 Hz, 1H), 1.30 (d, J=5.7 Hz, 3H).

Workup

  1. stirringthe reaction was stirred for 2 h
  2. stirringthe reaction was stirred for 10 min
  3. customThe layers were separated
  4. washthe organic layer was washed with 1M citric acid solution twice
  5. addition7 ml of water was added
  6. stirringAfter stirring for 1 h the layers
  7. customwere separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washThe combined organics were washed twice with 1M citric acid solution and twice with water
  10. additionIsopropanol (70 ml) was then added
  11. customthe solvents were evaporated slowly
  12. customleaving mostly isopropanol

Sources & evidence

ORD record
ord-c27ef4d9edcc439f98ef41269b35b09c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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