Cysteamine → Hexane isopropyl acetate

HRID 728999Notes

Reaction equation

HRID 728999 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8]C[CH2:10][CH2:11][O:12][C:13]2[CH:20]=CC(C=O)=C[CH:14]=2)ON=1.NCCS.C1(C)C=CC(S(O)(=O)=[O:32])=CC=1>C1(C)C=CC=CC=1>[C:11]([O:12][CH:13]([CH3:20])[CH3:14])(=[O:32])[CH3:10].[CH3:8][CH2:7][CH2:5][CH2:6][CH2:2][CH3:1]

Participants

5

Reactant 3

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

Product 1

HCID 22034165Hexane isopropyl acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.00 g of 4-[5-(3-methyl-5-isoxazolyl)pentyloxy]benzaldehyde (part a above), 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 recrystallizedfrom 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

Sources & evidence

ORD record
ord-3da514e9c10c487d9f52cc741bdd9bb1
Source dataset
uspto-grants-1991_09
Patent number
US05051437

Reaction notes

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