Piperidine → 5-(4-beta-D-Galactopyranosyloxy-3-methoxyphenylmethylene)-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one

HRID 1588198Notes

Reaction equation

HRID 1588198 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][S:10][C:9]2=[S:14])=[CH:4][CH:3]=1.[O:15]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][C:28]=1[O:35][CH3:36])[C@H:16]1[O:24][C@H:23]([CH2:25][OH:26])[C@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]1[OH:18].N1CCCCC1>CO>[C@@H:16]1([O:15][C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[C:11]3[S:10][C:9](=[S:14])[N:8]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=4)[C:12]3=[O:13])=[CH:29][C:28]=2[O:35][CH3:36])[O:24][C@H:23]([CH2:25][OH:26])[C@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]1[OH:18]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2105913-(4-Hydroxyphenyl)-2-thioxo-4-thiazolidinoneHCID 115151674-O-(alpha-d-galactopyranosyl)vanillin

Product 1

HCID 538827195-(4-beta-D-Galactopyranosyloxy-3-methoxyphenylmethylene)-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Hydroxyphenyl)-2-thioxothiazolidin-4-one (0.23 g, 1.0 mmol) was added to a suspension of 4-formyl-2-methoxyphenyl β-D-galactopyranoside (1c)(0.32 g, 1.0 mmol) in methanol (20 ml) containing a drop of piperidine. The mixture, which rapidly turned yellow, was gently heated under reflux and deposited a thick precipitate after 30 min. The mixture was then cooled and filtered to give the required product (5c){0.12 g, 23%, m.p. decomp.>230° C., [α]D -34.4° (c 0.6, DMOS)}(Found: C, 53.04; H, 4.55; N, 2.81. C23H23NO9S2 requires C, 52.96; H, 4.44; N, 2.68%).

Workup

  1. temperatureThe mixture, which rapidly turned yellow, was gently heated
  2. temperatureunder reflux
  3. customafter 30 min
  4. temperatureThe mixture was then cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c4a08aa3eff0472f92224978bc077c41
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

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