Iodoethanol → HCID 77845130, compound

HRID 1774084Notes

Reaction equation

HRID 1774084 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17](/[CH:21]=[CH:22]/[C:23]3[C:24]4[C:29]([N:30]=[C:31]5[C:36]=3[CH:35]=[CH:34][CH:33]=[CH:32]5)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.[I:37][CH2:38][CH2:39][OH:40]>C(#N)C>[I-:37].[OH:40][CH2:39][CH2:38][N+:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:23](/[CH:22]=[CH:21]/[C:17]2[CH:18]=[CH:19][C:20]3[N:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:9]4[C:14]([C:15]=3[CH:16]=2)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[C:24]2[C:29]=1[CH:28]=[CH:27][CH:26]=[CH:25]2

Participants

4

Reactant 2

HCID 12225IodoethanolHCID 86672680HCID 86672680, compound

Product 1

HCID 77845130HCID 77845130, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 12 (0.2 g, 0.4 mmol) and 2-iodoethanol (0.7 g, 4 mmol) in acetonitrile (10 mL) was heated to 120° C. in sealed tube for 24 h. After cooling down to room temperature, the solvent was removed and the resulting mixture was purified by precipitation from methanol and ethyl acetate to afford SAOH (0.13 g) in 52% yield. 1H NMR (400 MHz, CDCl3) δ 8.98 (d, J=9.2 Hz, 2H), 8.77 (d, J=8.4 Hz, 2H), 8.44 (s, 1H), 8.36 (t, J=8.0 Hz, 2H), 8.18 (d, J=8.4 Hz, 1H), 8.17 (d, J=16 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.86 (t, J=8.0 Hz, 2H), 7.62 (d, J=8.8 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.52 (t, J=6.4 Hz, 2H), 7.48 (d, J=16 Hz, 1H), 7.33 (t, J=6.4 Hz, 1H), 5.63 (t, J=6.0 Hz, 2H), 4.75 (t, J=7.6 Hz, 1H), 4.59 (t, J=6.0 Hz, 2H), 4.51-4.47 (m, 2H), 3.94 (t, J=6.0 Hz, 2H), 3.57-3.55 (m, 2H), 3.47-3.44 (m, 2H), 3.33 (s, 3H). 13C NMR (400 MHz, CDCl3) δ 158.2, 149.1, 141.9, 140.7, 140.6, 138.1, 129.1, 126.9, 126.5, 126.4, 124.3, 123.3, 122.4, 121.2, 120.9, 120.0, 119.0, 117.0, 109.6, 109.2, 71.8, 70.6, 69.1, 59.3, 58.9, 52.2, 43.3. HRMS (MALDI-TOF) m/z Calcd for C34H33N2O3+ 517.2486 Found 517.2476 [M]+.

Workup

  1. customthe solvent was removed
  2. customthe resulting mixture was purified by precipitation from methanol and ethyl acetate
  3. customto afford SAOH (0.13 g) in 52% yield

Sources & evidence

ORD record
ord-e98ecb542c0845d79eba981161181ee1
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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