Hydrochloric Acid → HCID 68601215, compound

HRID 1799676Notes

Reaction equation

HRID 1799676 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[N:8]=[CH:9][S:10][C:11]=1/[CH:12]=[CH:13]\[S:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6].Cl.C(OCC)(=O)C>C1COCC1.O>[C:5]([C:7]1[N:8]=[CH:9][S:10][C:11]=1/[CH:12]=[CH:13]\[S:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:6])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 68599048HCID 68599048, compound

Product 1

HCID 68601215HCID 68601215, compoundYield 117.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 5 N aqueous sodium hydroxide solution (8.30 ml) was added to a suspension of 7.31 g of 4-methoxycarbonyl-5-((Z)-2-tritylthioethen-1-yl)thiazole in THF, and the mixture was stirred at 60° C. for one hr. The mixture was then cooled to room temperature, and 8.50 ml of 5 N hydrochloric acid, 100 ml of ethyl acetate, and 50 ml of water were added thereto, followed by concentration to 150 ml. Hexane (100 ml) was added to the concentrate, and the precipitated solid was collected by filtration and was washed with ethyl acetate-hexane (2:1) to give 8.30 g of 4-carboxy-5-((Z)-2-tritylthioethen-1-yl)thiazole.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationfollowed by concentration to 150 ml
  3. additionHexane (100 ml) was added to the concentrate
  4. filtrationthe precipitated solid was collected by filtration
  5. washwas washed with ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-4a6fcd269d4746ccbff1ccc7bae1eb3b
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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