Diethyl Ether → (4-Methoxyphenyl)methyl carbamimidothioate

HRID 1106629Notes

Reaction equation

HRID 1106629 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][CH:8]=1.CCOCC>O1CCCC1>[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][S:3][C:2](=[NH:4])[NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 699934-Methyloxybenzyl chlorideHCID 2723790Thiourea

Product 1

HCID 415139(4-Methoxyphenyl)methyl carbamimidothioateYield 116.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of thiourea (3.8 g, 50.0 mmol) in tetrahydrofuran (30 mL) was added dropwise 4-methoxybenzyl chloride (8.0 g, 51.1 mmol) and the reaction mixture was stirred at room temperature for 2 h before heating to reflux for 4 h. After the reaction was stirred at room temperature for 18 h the product was isolated from ether to yield the title compound (11.46 g). Electrospray MSm /z 197 [M+H]+.

Workup

  1. temperaturebefore heating
  2. temperatureto reflux for 4 h
  3. stirringAfter the reaction was stirred at room temperature for 18 h the product

Sources & evidence

ORD record
ord-71d43a8006d5434fbbab55454363eed0
Source dataset
uspto-grants-2000_05
Patent number
US06057332

Reaction notes

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