Cysteamine → 3-Methyl-5-{5-[4-(2-thiazolidinyl)phenoxy]pentyl}isoxazole

HRID 1722763Notes

Reaction equation

HRID 1722763 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)[O:4][N:3]=1.[NH2:21][CH2:22][CH2:23][SH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]3[NH:21][CH2:22][CH2:23][S:24]3)=[CH:15][CH:14]=2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 6058CysteamineHCID 6101p-Toluenesulfonic acidHCID 64834254-[5-(3-Methyl-5-isoxazolyl)pentyloxy]benzaldehyde

Product 1

HCID 542310383-Methyl-5-{5-[4-(2-thiazolidinyl)phenoxy]pentyl}isoxazoleYield 39.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.00 g of 4-[5-(3-methyl-5-isoxazolyl)pentyloxy]benzaldehyde (Example 35a), 1.22 g of 2-aminoethanethiol and a trace of p-toluenesulfonic acid in 30 ml of toluene was heated at reflux for 2 hours using a Dean-Stark trap. The product was isolated and recrystallized from isopropyl acetate-hexane to give 1.93 g of the above-indicated product, m.p. 82-84° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe product was isolated
  3. customrecrystallized from isopropyl acetate-hexane

Sources & evidence

ORD record
ord-31b7c2b1b09d4e349e8ff3afac464ce9
Source dataset
uspto-grants-1989_08
Patent number
US04857539

Reaction notes

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