Dimethylamine → 1,1-Dimethyl-3-(3-methyl-but-2-enoyl)-thiourea

HRID 1054929Notes

Reaction equation

HRID 1054929 reaction equation
[CH3:1][C:2]([CH3:9])=[CH:3][C:4]([N:6]=[C:7]=[S:8])=[O:5].[CH3:10][NH:11][CH3:12].C1COCC1>>[CH3:10][N:11]([CH3:12])[C:7]([NH:6][C:4](=[O:5])[CH:3]=[C:2]([CH3:9])[CH3:1])=[S:8]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 900170793-Methylbut-2-enoyl isothiocyanate

Product 1

HCID 900165521,1-Dimethyl-3-(3-methyl-but-2-enoyl)-thioureaYield 84.9%

Procedure

Was prepared in the same manner as described in General Procedure Example 1b) using 3-methylbut-2-enoyl isothiocyanate (2 g, 14.2 mmol, Eq: 1.00) and dimethylamine solution 2M in THF (7.08 ml, 14.2 mmol, Eq: 1.00). Evaporation of the solvent afforded 1,1-dimethyl-3-(3-methyl-but-2-enoyl)-thiourea (2.239 g/84.9%) as a yellow oil which was used without further purification in the next step. MS: m/e=187.4 (M+H+)

Workup

  1. customWas prepared in the same manner
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d47f00a86e5344428d015de252a2927e
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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