Water → 2,2'-([1,3]Thiazolo[5,4-d][1,3]thiazole-2,5-diyl)diphenol

HRID 1974820Notes

Reaction equation

HRID 1974820 reaction equation
[NH2:1][C:2]([C:4]([NH2:6])=[S:5])=[S:3].[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O.[OH2:16]>C(O)C.CCOCC>[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]1[S:3][C:2]2[N:1]=[C:10]([C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[OH:16])[S:5][C:4]=2[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6998Salicylaldehyde2×HCID 2777982Dithiooxamide

Product 1

HCID 2409212,2'-([1,3]Thiazolo[5,4-d][1,3]thiazole-2,5-diyl)diphenolYield 50%

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

Into a 100 ml round bottomed flask equipped with heating mantle and magnetic stirrer, were added 2.0 g (0.017 mol) of dithiooxamide (DTO) and 21 g (0.17 mol--a tenfold excess) of o-hydroxybenzaldehyde (salicylaldehyde). The salicylaldehyde was purchased from Eastman Organic Chemicals Division of Eastman Kodak Company, Rochester, N.Y. The mixture was stirred and heated at 180°-185° C. for 2 hr. At 160° C. water began to boil off. After 2 hr, the reaction mixture was cooled to room temperature and 50 ml of ethanol/ether 1:1 were added. Stirring for 10 min was followed by filtration to remove the product. The product was washed with ethanol and dried in air overnight to afford 2.9 g (50%) of 2,5-bis(o-hydroxyphenyl)thiazolo[5,4-d]thiazole, mp 300° C. NMR and IR were in agreement with the assigned structure.

Workup

  1. customInto a 100 ml round bottomed flask equipped
  2. temperaturewith heating mantle and magnetic stirrer
  3. temperatureheated at 180°-185° C. for 2 hr
  4. customAt 160° C.
  5. stirringStirring for 10 min
  6. filtrationwas followed by filtration
  7. customto remove the product
  8. washThe product was washed with ethanol
  9. customdried in air overnight

Sources & evidence

ORD record
ord-8ab04052fce44d6bbab26a29738b02bc
Source dataset
uspto-grants-1994_02
Patent number
US05284812

Reaction notes

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