Aniline → HCID 58078887, compound

HRID 532088Notes

Reaction equation

HRID 532088 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]#[CH:20])(=O)=O)=CC=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:18]([O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19]#[CH:20]

Participants

3

Reactant 2

HCID 6115AnilineHCID 25199393HCID 25199393, compound

Product 1

HCID 58078887HCID 58078887, compoundYield 53.1%

Procedure

2-(2-(prop-2-ynyloxy)ethoxy)ethyl 4-methylbenzenesulfonate (s-8)2 (100 mg, 0.335 mmol, 0.31 equiv.) was dissolved in aniline (102 mg, 1.10 mmol, 1 equiv.). The reaction was allowed to proceed at 100° C. in a sealed reaction vessel for 5 hours, after which time it was chromatographed (Silica Gel, 25 g RediSep pre-packed column, 0% EtOAc:Hexanes→20% EtOAc:Hexanes) to yield N-(2-(2-(prop-2-ynyloxy)ethoxy)ethyl)aniline (s-9) as a brown oil (39.0 mg, 53.1%). IR (thin film) 3393 (m), 3278 (m), 3052 (w), 2865 (m), 2115 (w), 1603 (s), 1506 (s), 1461 (w), 1320 (w), 1277 (m), 1099 (s), 1030 (w), 750 (s), 693 (s); 1H NMR (500 MHz, CDCl3) δ 7.22-7.16 (m, 2H), 6.72 (t, J=7.3 Hz, 1H), 6.67-6.63 (m, 2H), 4.22 (d, J=2.4 Hz, 2H), 4.12 (s, 1H), 3.74-3.70 (m, 4H), 3.70-3.66 (m, 2H), 3.32 (t, J=5.2 Hz, 2H), 2.46 (t, J=2.4 Hz, 1H). 13C NMR (125 MHz, CDCl3) 148.7, 129.6, 117.9, 113.5, 80.0, 75.1, 70.5, 70.1, 69.5, 58.9, 43.9. HRMS (ES+) calc'd for C13H17NO2 (M+H) m/z 220.1293 Found 220.1327.

Workup

  1. customto proceed at 100° C. in a sealed reaction vessel for 5 hours
  2. customafter which time it was chromatographed (Silica Gel, 25 g RediSep pre-packed column, 0% EtOAc:Hexanes→20% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-cf51cb9978f741b68391254d8f3b0ea2
Source dataset
uspto-grants-2014_10
Patent number
US08852630B2

Reaction notes

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