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

HRID 839922Notes

Reaction equation

HRID 839922 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-thiazolyl-acetate, 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 decanted and 5 ml of N hydrochloric acid and 5 ml of water were again added. The mixture was decanted and the organic phase was dried and evaporated 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 stood overnight at room temperature. The mixture was evaporated to dryness 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 was allowed to crystallize and was then vacuum filtered to obtain 1.33 g of 2-tritylamino-4-thiazolyl-acetic acid which after empasting with ether melted at 220° C.

Workup

  1. stirringThe mixture was stirred
  2. customdecanted
  3. addition5 ml of N hydrochloric acid and 5 ml of water were again added
  4. customThe mixture was decanted
  5. customthe organic phase was dried
  6. customevaporated 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. waitstood overnight at room temperature
  10. customThe mixture was evaporated to dryness
  11. additionthe residue was diluted with water
  12. washThe solution was washed with ether
  13. customto crystallize
  14. filtrationvacuum filtered

Sources & evidence

ORD record
ord-29efc93e7c19478e9ac9c3cca9ee00c5
Source dataset
uspto-grants-1978_06
Patent number
US04097595

Reaction notes

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