2-Thiophenecarboxaldehyde → HCID 178496316, compound

HRID 845579Notes

Reaction equation

HRID 845579 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][OH:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH:35]=O>>[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21](=[O:22])=[CH:35][C:31]3[S:30][CH:34]=[CH:33][CH:32]=3)[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9]

Participants

3

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 14183058HCID 14183058, compound

Product 1

HCID 178496316HCID 178496316, compoundYield 86.5%

Procedure

The reaction of hydroxylamine 55 (0.80 g, 2 mmol) with 2-thiophenecarboxaldehyde (64) (0.224 g, 2 mmol) afforded, after workup, a light yellow oil. The crude product was purified by flash chromatography with 2:1 ethyl acetate/hexane as the eluant to obtain 0.86 g (1.73 mmol, 86%) of 75 as a yellow gum: IR (CH2Cl2) 3440, 2940, 1698, 1625, 1560, 1472, 1375, 1298, 1215, 1105, cm-1 ; 1H NMR (CDCl3) δ 1.09 (d, J=6.2 Hz, 3H), 1.21 (d, J=6.2 Hz, 3H), 2.28 (s, 6H), 3.32 (s, 3H), 3.56 (t, J=4.8 Hz, 2H), 4.18 (m, 2H), 4.94 (septet, J=6.2 Hz, 1H), 5.09 (s, 1H), 6.99-8.52 (m, 8H); 13C NMR (CDCl3) δ 19.32, 19.44, 21.99, 22.22, 40.12, 58.85; 62.81, 67.18, 70.74, 102.75, 103.53, 118.83, 120.88, 127.19, 128.53, 129.34, 130.21, 130.29, 131.42, 133.00, 145.12, 145.91, 146.37, 149.97, 167.09, 167.55. Anal. calcd for C26H30N2O6S: C, 62.65; H, 6.02. Found: C, 62.47; H, 6.10.

Workup

  1. customafforded
  2. customThe crude product was purified by flash chromatography with 2:1 ethyl acetate/hexane as the eluant

Sources & evidence

ORD record
ord-0eccd07391194e95833e249deebd40d3
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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