Tetrahydrofuran → 2-Amino-N-(prop-2-yn-1-yl)benzamide

HRID 1687745Notes

Reaction equation

HRID 1687745 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.O1CCCC1.[CH2:18]([NH2:21])[C:19]#[CH:20]>>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:21][CH2:18][C:19]#[CH:20])=[O:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8359Isatoic AnhydrideHCID 239041Propargylamine

Product 1

HCID 27644242-Amino-N-(prop-2-yn-1-yl)benzamideYield 100%

Procedure

Isatoic Anhydride (4.00 g, 24.5 mmol) was dissolved in tetrahydrofuran (100 mL, 1.230 mol) at 0° C. Prop-2-ynylamine (2.52 mL, 36.8 mmol) was added and the reaction was stirred for 2 hours and then concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-50% EtOAc/hex as the eluting solvent to obtain 2-amino-N-prop-2-ynyl-benzamide as a white solid (4.27 g, 100%). m.p.=75° C.; LCMS (m/e) 120 (M—NHCH2CCH); 1H-NMR (CDCl3, 400 MHz) δ 7.35 (d, 1H, J=7.9 Hz), 7.24 (dd, 1H, J=7.3 and 8.2 Hz), 6.73-6.64 (m, 2H), 6.19 (bs, 1H), 5.56 (bs, 2H), 4.26-4.20 (m, 2H), 2.29 (t, 1H, J=1.5 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-d28a649d5830493a8e7540ad19fda61e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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