Isobutyl isothiocyanate → 1-[(2,4-Dimethoxybenzoyl)amino]-3-(2-methylpropyl)thiourea

HRID 10732

Reaction equation

HRID 10732 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[C:5]([NH:7][NH2:8])=[O:6].[CH2:15]([N:19]=[C:20]=[S:21])[CH:16]([CH3:18])[CH3:17]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[C:5]([NH:7][NH:8][C:20]([NH:19][CH2:15][CH:16]([CH3:18])[CH3:17])=[S:21])=[O:6]

Participants

4

Reactant 2

HCID 68960Isobutyl isothiocyanateHCID 4567282,4-Dimethoxybenzohydrazide

Product 1

HCID 22084281-[(2,4-Dimethoxybenzoyl)amino]-3-(2-methylpropyl)thioureaYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ex-109B: A solution of 2,4-dimethoxy-benzoic acid hydrazide (Ex-109A, 1.0 g, 5.1 mmol) and isobutyl-isothiocyanate (0.70 g, 6.1 mmol) in ethanol (30 mL) was refluxed for 8 hours. The precipitate was filtered, washed with ethanol, dried in vacuo to afford 1-(2,4-dimethoxy-benzoyl)amino-3-isobutyl-thiourea (1.43 g). Additional product (0.1 g, 96% overall) was obtained by concentrating the mother liquid. 1H NMR (CDCl3) δ 10.71 (bs, 1H), 9.23 (bs, 1H), 8.03 (d, J=8.6 Hz, 1H), 6.98 (bs, 1H), 6.59 (dd, J=8.6, 2.6 Hz, 1H), 6.51 (d, J=2.6 Hz, 1H), 4.02 (s, 3H), 3.86 (s, 3H), 3.41 (dd, J=6.4, 6.6 Hz, 2H), 1.96–1.87 (m, 1H), 0.91 (d, J=6.5 Hz, 6H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-8128df313cf4428687143d608ab819d6
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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