Hydrochloric Acid → HCID 68601215, compound

HRID 2246077Notes

Reaction equation

HRID 2246077 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-41cdf6633c7b49fe94280a259a0a68ec
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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