Morpholine → HCID 178512094, compound

HRID 971878Notes

Reaction equation

HRID 971878 reaction equation
I.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:9][C:10](=[NH:13])SC)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.Cl[O-].[Na+].[OH-].[Na+]>C(O)(C)(C)C>[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:9][C:10]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[NH:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 14798Sodium Hydroxide2×HCID 23665760Sodium HypochloriteHCID 178504030HCID 178504030, compound

Product 1

HCID 178512094HCID 178512094, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1-(Diphenylmethyl)-2-methyl-2-thiopseudourea hydriodide (19.2 g., 0.05 mole) in 75 ml. tert-butanol is heated at reflux for 24 hours with morpholine (8.7 g., 0.1 mole) under a slow stream of nitrogen. The effluent gas is passed through sodium hypochlorite and sodium hydroxide traps to remove the methyl mercaptan formed in the reaction. The mixture was taken to dryness in vacuo and the residue was treated with 3 N sodium hydroxide. Extraction with methylene chloride, washing the combined extracts with water, drying over potassium carbonate, filtration and solvent removal under reduced pressure furnishes an oil which solidifies on standing. Recrystallization several times from acetone-ether gives N-(diphenylmethyl)-4-morpholinecarboximidamide as a white solid; mp 122°-124° C.

Workup

  1. customto remove the methyl mercaptan
  2. customformed in the reaction
  3. extractionExtraction with methylene chloride
  4. washwashing the combined extracts with water
  5. dry with materialdrying over potassium carbonate, filtration and solvent removal under reduced pressure
  6. customfurnishes an oil which
  7. customRecrystallization several times from acetone-ether

Sources & evidence

ORD record
ord-2b19cfc6b3594f0d871c3ad97fd9ce56
Source dataset
uspto-grants-1979_07
Patent number
US04161541

Reaction notes

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