3-(4-Hydroxyphenyl)-2-thioxo-4-thiazolidinone → 5-[4-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-3-methoxyphenylmethylene]-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one

HRID 1588196Notes

Reaction equation

HRID 1588196 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.[C:15]([NH:18][C@@H:19]1[C@@H:35]([OH:36])[C@H:34]([OH:37])[C@@H:33]([CH2:38][OH:39])[O:32][C@H:20]1[O:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][C:23]=1[O:30][CH3:31])(=[O:17])[CH3:16].C([O-])(=O)C.[NH4+]>C(O)C>[C:15]([NH:18][C@@H:19]1[C@@H:35]([OH:36])[C@H:34]([OH:37])[C@@H:33]([CH2:38][OH:39])[O:32][C@H:20]1[O:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[C:11]2[S:10][C:9](=[S:14])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[C:12]2=[O:13])=[CH:24][C:23]=1[O:30][CH3:31])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 2105913-(4-Hydroxyphenyl)-2-thioxo-4-thiazolidinoneHCID 517165Ammonium AcetateHCID 52931324-Formyl-2-methoxyphenyl 2-acetamido-2-deoxy-beta-glucopyranoside

Product 1

HCID 541642225-[4-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-3-methoxyphenylmethylene]-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-oneYield 82.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Hydroxyphenyl)-2-thioxothiazolidin-4-one (0.23 g, 1.0 mmol) was added to a stirred suspension of 4-formyl-2-methoxyphenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (1b)(0.32 g, 0.9 mmol) in absolute ethanol (10 ml) containing ammonium acetate (0.08 g, 1.0 mmol) and the pale yellow heterogeneous reaction mixture boiled gently. After 5 h the mixture was cooled in ice and the yellow product was filtered off and washed well with methanol and acetone to give 5b (0.42 g, 74%), m.p. 234°-236° C., [α]D +2.5° (c 0.81, DMOS) Found: C, 53.62; H, 4.65; N, 4.73, C25H26N2O9S2 calc: C, 53.38; H, 4.63; N, 4.98).

Workup

  1. temperatureAfter 5 h the mixture was cooled in ice
  2. filtrationthe yellow product was filtered off
  3. washwashed well with methanol and acetone

Sources & evidence

ORD record
ord-6bc9ca75b9614fb4849c1a02f257f1ea
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

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