Diethyl Ether → 2-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-3-methylbenzothiazolium tosylate

HRID 1588206Notes

Reaction equation

HRID 1588206 reaction equation
[O:1]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:14]=1[O:21][CH3:22])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[S:23]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([O-:26])(=[O:25])=[O:24].[CH3:34][C:35]1[S:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[N+:39]=1[CH3:40].N1CCCCC1.CCOCC>CO>[S:23]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([O-:26])(=[O:25])=[O:24].[C@@H:2]1([O:1][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH:34][C:35]3[S:36][C:37]4[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=4[N+:39]=3[CH3:40])=[CH:15][C:14]=2[O:21][CH3:22])[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 102307Benzothiazolium, 2,3-dimethyl-, 4-methylbenzenesulfonate (1:1)HCID 115151674-O-(alpha-d-galactopyranosyl)vanillin

Product 1

HCID 1317179912-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-3-methylbenzothiazolium tosylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Formyl-3-methoxyphenyl β-D-galactopyranoside (1c)(3.14 g, 0.01 mol) was dissolved in hot methanol (20 ml) and 2,3-dimethylbenzothiazolium tosylate (3.35 g, 0.01 mol) was added followed by a drop of piperidine. The mixture was heated under reflux for 2 h, during which time it become strongly coloured. The reaction mixture was then cooled and ether (200 ml) was added to precipitate the product as an orange solid, which was well washed with methanol to give (26c){4.8 g, 80%, m.p. 147°-149° C., [α]D -10.4`0 (c 1, DMSO)}. (Found: C, 55.66; H, 5.28; N, 2.11. C30H34O11NS2Calc: C, 55.54; N, 5.28; N, 2.16.)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h, during which time it
  3. temperatureThe reaction mixture was then cooled
  4. customto precipitate the product as an orange solid, which
  5. washwas well washed with methanol

Sources & evidence

ORD record
ord-da2061ed91764e9eb69ccf76acc58a27
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

Loading…