Propargylamine → HCID 58956310, compound

HRID 1853435Notes

Reaction equation

HRID 1853435 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11](Cl)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:15]([NH2:18])[C:16]#[CH:17]>C(OCC)(=O)C.O>[CH2:15]([NH:18][S:11]([CH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:13])=[O:12])[C:16]#[CH:17]

Participants

5

Reactant 2

HCID 239041PropargylamineHCID 2794642(4-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 58956310HCID 58956310, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a cooled (0° C.) suspension of 4-nitrophenylmethanesulfonylchloride (0.510 g, 2.16 mmol) in ethyl acetate (3.0 mL) was added a solution of propargyl amine (1.0 mL, 14.5 mmol) in water (1.0 mL). The reaction mixture was stirred for 30 minutes and then diluted with ethyl acetate (30 mL) and washed with 1N HCl (10 mL), water (10 mL), and brine (10 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to provide 4-(prop-2-ynylaminosulfonylmethyl)nitrobenzene as a tan solid (0.437 g), which was used without further purification. 1HNMR (CDCl3): δ 8.25 (d, J=8.7 Hz, 2H), 7.66 (d, J=8.7 Hz, 2H), 4.48 (s, 3H), 3.98 (dd, J=2.7 and 6.3 Hz, 2H), 2.48 (t, J=2.7 Hz, 1H); LCMS: purity: 99%; MS (m/e): 253 (M−).

Workup

  1. temperatureTo a cooled
  2. washwashed with 1N HCl (10 mL), water (10 mL), and brine (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd58e0c104044834bc81a4fc3c22c7bf
Source dataset
uspto-grants-2015_02
Patent number
US08962643B2

Reaction notes

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