Acetic Acid → HCID 59292311, compound

HRID 1685112Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].C(O)(=O)C.[O-:18][C:19]#[N:20].[K+]>O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([NH:10][C:19]([NH2:20])=[O:18])[CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask containing 3-(3-methoxypropoxy)aniline (11A) (2.00 g, 11.04 mmol) was charged a 100 mL solution of 80% glacial acetic acid and 20% water. This mixture was chilled to 0° C. A solution of potassium cyanate (1.34 g, 16.56 mmol) in 5 mL of water was slowly added portion-wise to the reaction mixture. The reaction was then stirred for about 1 hour at RT. The glacial acetic acid was then removed under reduced pressure. The resulting white solid residue was then rinsed with copious amounts of water then dried under vacuum to give title compound 11B (1.70 g, 70%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.86-1.95 (m, 2H) 3.24 (s, 3H) 3.46 (t, J=6.32 Hz, 2H) 3.94 (t, J=6.32 Hz, 2H) 5.82 (br. s., 2H) 6.45 (dd, J=8.08, 2.27 Hz, 1H) 6.81 (d, J=7.33 Hz, 1H) 7.00-7.17 (m, 2H) 8.49 (s, 1H). ESI-MS: m/z 225.3 (M+H)+.

Workup

customThe glacial acetic acid was then removed under reduced pressure
washThe resulting white solid residue was then rinsed with copious amounts of water
customthen dried under vacuum

Sources & evidence

ORD record: ord-b92b920332964f42b4f5f5638bd9f7d4
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148367B2

Reaction notes

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