Sodium Hydroxide → 4-Morpholinecarbothioamide

HRID 541344Notes

Reaction equation

HRID 541344 reaction equation
[N:1]1([C:7]([NH:9]C(=O)C2C=CC=CC=2)=[S:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[N:1]1([C:7](=[S:8])[NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 696258N-(Morpholine-4-carbothioyl)benzenecarboximidic acid2×

Product 1

HCID 23935444-Morpholinecarbothioamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a round-bottom flask was added a solution of N-(morpholine-4-carbonothioyl)benzamide (compound 211.9, 3.00 g, 12.0 mmol, 1.00 equiv) in methanol (20 mL). A solution of sodium hydroxide (1.44 g, 36.0 mmol, 3.00 equiv) in water (20 mL) was added to the reaction. The resulting solution was stirred overnight at 60° C. After cooling to ambient temperature, the organic solvent was removed under reduced pressure. The residue was extracted with 2×20 mL of ethyl acetate/petroleum ether(1:1). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 430 mg (25%) of morpholine-4-carbothioamide as a yellow solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe organic solvent was removed under reduced pressure
  3. extractionThe residue was extracted with 2×20 mL of ethyl acetate/petroleum ether(1:1)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThis resulted in 430 mg (25%) of morpholine-4-carbothioamide as a yellow solid

Sources & evidence

ORD record
ord-54552dedb4b64013b3207abccca74f56
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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