Sodium Hydroxide → HCID 12799746, compound

HRID 1446950Notes

Reaction equation

HRID 1446950 reaction equation
[CH3:1][C:2]([O:7][CH3:8])([CH3:6])[C:3](O)=O.[NH2:9][NH:10][C:11]([NH2:13])=[S:12].P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C(OCC)C.O.O1CCOCC1>[CH3:8][O:7][C:2]([C:3]1[S:12][C:11]([NH2:13])=[N:10][N:9]=1)([CH3:6])[CH3:1]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride2×HCID 2723789ThiosemicarbazideHCID 98554652-methoxy-2-methylpropanoic acid

Product 1

HCID 12799746HCID 12799746, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

Into a 150 milliliter, 3-neck flask equipped with a Claisen adaptor, paddle stirrer, thermometer, addition funnel and condenser were charged 7.1 grams (0.060 mole) of 2-methyl-2-methoxypropanoic acid, prepared above, (5.5 grams, 0.060 mole) of thiosemicarbazide and 50 milliliters of dry dioxane. The slurry was heated to 85° C. and the addition funnel was charged with phosphorous oxychloride (POCl3). The POCl3 (10.1 grams, 0.066 mole) was slowly added (for 20 minutes) while maintaining the temperature within 85°-95° C. The resulting suspension was refluxed for 1 hour and topped slightly with a water aspirator and then cooled. Fifty (50) milliliters of water was added and 50% solution of NaOH was also added until the pH of the solution was 10; an aqueous phase formed. The mixture was placed in a continuous diethylether extractor and extracted for 16 hours.

Workup

  1. customInto a 150 milliliter, 3-neck flask equipped with a Claisen adaptor, paddle stirrer
  2. additionthermometer, addition funnel and condenser
  3. temperaturewhile maintaining the temperature within 85°-95° C
  4. temperatureThe resulting suspension was refluxed for 1 hour
  5. temperaturecooled
  6. customan aqueous phase formed
  7. extractionextracted for 16 hours

Sources & evidence

ORD record
ord-4aab307aaf6d444b8ef1f4d3871aa468
Source dataset
uspto-grants-1982_02
Patent number
US04314842

Reaction notes

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