Hydrochloric Acid → {2-[(Triphenylmethyl)amino]-1,3-thiazol-4-yl}acetic acid

HRID 1395694Notes

Reaction equation

HRID 1395694 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10]CC)=[O:9])[N:6]=1.C(Cl)(Cl)Cl.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O.C(N(CC)CC)C>[C:17]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 6456Trityl chlorideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 13631022{2-[(Triphenylmethyl)amino]-1,3-thiazol-4-yl}acetic acidYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 930 mg of ethyl 2-amino-4-thiazolylacetate, 25 ml of dry chloroform, 0.8 ml of triethylamine and 1.65 g of trityl chloride was stirred for 3 hours and then 3 ml of N hydrochloric acid and 5 ml of water were added thereto. The mixture was stirred and was decanted and another 3 ml of N hydrochloric acid and 5 ml of water were added to the organic phase. The mixture was decanted and the organic phase was dried and concentrated to dryness. The residue was added to 10 ml of dioxane and 6 ml of N sodium hydroxide and the mixture was stirred at 50° C. and then overnight at room temperature. The solvent was evaporated and the residue was diluted with water. The solution was washed with ether and was acidified with 0.5 ml of acetic acid. The mixture crystallized and was vacuum filtered to obtain 1.33 g of 2-tritylamino-4-thiazolyl-acetic acid which after purification by empasting with ether melted at 220° C.

Workup

  1. stirringThe mixture was stirred
  2. customwas decanted
  3. additionanother 3 ml of N hydrochloric acid and 5 ml of water were added to the organic phase
  4. customThe mixture was decanted
  5. customthe organic phase was dried
  6. concentrationconcentrated to dryness
  7. additionThe residue was added to 10 ml of dioxane and 6 ml of N sodium hydroxide
  8. stirringthe mixture was stirred at 50° C.
  9. customovernight
  10. customat room temperature
  11. customThe solvent was evaporated
  12. additionthe residue was diluted with water
  13. washThe solution was washed with ether
  14. customThe mixture crystallized
  15. filtrationfiltered

Sources & evidence

ORD record
ord-1a30f90f36834dca84af8c0d1770f6c1
Source dataset
uspto-grants-1980_05
Patent number
US04205072

Reaction notes

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