Pyrrolidine → 3-methyl-N-(pyrrolidine-1-carbonothioyl)but-2-enamide

HRID 1054922Notes

Reaction equation

HRID 1054922 reaction equation
[CH3:1][C:2]([CH3:9])=[CH:3][C:4]([N:6]=[C:7]=[S:8])=[O:5].[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>C1C=CC=CC=1>[N:10]1([C:7]([NH:6][C:4](=[O:5])[CH:3]=[C:2]([CH3:9])[CH3:1])=[S:8])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 900170793-Methylbut-2-enoyl isothiocyanate

Product 1

HCID 900178533-methyl-N-(pyrrolidine-1-carbonothioyl)but-2-enamideYield 110%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3-methylbut-2-enoyl isothiocyanate (500 mg, 3.54 mmol, Eq: 1.00) in benzene (10.0 ml) was added a solution of pyrrolidine (252 mg, 293 μl, 3.54 mmol, Eq: 1.00) in benzene (5.00 ml). The mixture was stirred for 30 minutes. The solvent was evaporated affording 3-methyl-but-2-enoic acid (pyrrolidine-1-carbothioyl)-amide (824 mg/110%) as a light yellow solid. MS: m/e=213.1 (M+H+)

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-664f2c8615f6407f8566633b1e3f3ca3
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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