Morpholine → Ethyl (morpholin-4-ylcarbonothioyl)carbamate

HRID 2212245Notes

Reaction equation

HRID 2212245 reaction equation
[N:1]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]=[S:3].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C1COCC1>[CH2:7]([O:6][C:4](=[O:5])[NH:1][C:2]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[S:3])[CH3:8]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 2824559Ethyl (morpholin-4-ylcarbonothioyl)carbamateYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl isothiocyanatoformate (5 g, 38.2 mmol) was dissolved in THF (50 mL) and cooled to 0° C. Morpholine (3.99 mL, 45.8 mmol) was added dropwise over 2 min. The reaction mixture was stirred for 3 h. The solvent was evaporated to give (morpholin-4-yl-carbothioyl)carbamic acid ethyl ester (8.3 g, 38 mmol) as a white solid.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3a44acc91db84ee9b6403d0af4091683
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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