Tetrahydrofuran → Methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate

HRID 541301Notes

Reaction equation

HRID 541301 reaction equation
[C:1]([C:3]1[C:4]([CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:5][C:6]([CH2:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].O1CCCC1.P(OCC)(OCC)([S-])=[S:25]>O>[C:1]([C:3]1[C:4]([CH:15]2[CH2:16][CH2:17][CH2:18]2)=[CH:5][C:6]([CH2:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])(=[S:25])[NH2:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1385274Diethyl dithiophosphate, potassium saltHCID 68288744Methyl 5-cyano-4-cyclobutyl-2-ethylbenzoate2×

Product 1

HCID 86672532Methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoateYield 38.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round-bottom flask was added a solution of methyl 5-cyano-4-cyclobutyl-2-ethylbenzoate (compound 181.5, 3.00 g, 12.3 mmol, 1.00 equiv) in a solvent mixture of tetrahydrofuran and H2O (80 mL/40 mL). To this was added O,O′-diethyl dithiophosphate (6.69 g, 35.9 mmol, 3.00 equiv) dropwise with stirring. The resulting solution was stiffed at 85° C. for 48 h (CAUTION: significant gas evolution occurs—this and all other reactions described herein should be carried out in well ventilated fume hoods). After cooling to ambient temperature, the mixture was then concentrated in vacuo. The crude product was purified by re-crystallization from petroleum ether to furnish 1.30 g (38%) of methyl 5-carbamothioyl-4-cyclobutyl-2-ethylbenzoate as a light yellow solid.

Workup

  1. concentrationthe mixture was then concentrated in vacuo
  2. customThe crude product was purified by re-crystallization from petroleum ether

Sources & evidence

ORD record
ord-4262186ea80b404c89eba126a2134b40
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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