2-Thiophenecarboxaldehyde → HCID 178498417, compound

HRID 845587Notes

Reaction equation

HRID 845587 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][OH:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]=O>>[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18](=[O:19])=[CH:32][C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 14183059HCID 14183059, compound

Product 1

HCID 178498417HCID 178498417, compoundYield 71%

Procedure

The reaction of hydroxylamine 82 (0.71 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 1:1 ethyl acetate/petroleum ether as the eluant to obtain 0.64 g (1.41 mmol, 71%) of 87 as a light yellow oil. The oil crystallized from ether/pentane to yield yellow crystalline solid: mp 106°-109° C.; IR (CH2Cl2) 3440, 2940, 1695, 1620, 1555, 1470, 1375, 1300, 1215, 1100 cm-1 ; 1H NMR (CDCl3) δ 1.10 (d, J=6.2 Hz, 3H), 1.22 (d, J=6.2 Hz, 3H), 2.27 (s, 6H), 3.61 (s, 3H), 4.94 (septet, J=6.2 Hz, 1H), 5.06 (s, 1H), 6.98 (s, 1H), 7.17-7.77 (m, 7H), 8.44 (s, 1H); 13C NMR (CDCl3) δ 19.87, 22.49, 22.74, 40.59, 51.54, 67.68, 103.30, 104.00, 119.18, 121.52, 127.64, 128,95, 129.76, 130.60, 130.66, 131.78, 133.49, 145.64, 146.13, 147.07, 150.57, 167.62, 168.64. Anal. Calcd for C24H26N2O5S: C, 63.43; H, 5.72. Found: C, 63.26; H, 5.72.

Workup

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

Sources & evidence

ORD record
ord-dcfe4f4644854448a1c382ed9c473e51
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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