4-Nitrobenzyl bromide → Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromide

HRID 712352Notes

Reaction equation

HRID 712352 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Br:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1>CC(C)=O>[BrH:5].[C:2]([S:3][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=[NH:4])[NH2:1]

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 2723790Thiourea

Product 1

HCID 116350Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromideYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of thiourea (3.87 g, 50.92 mmol) in acetone (15 mL) was added a solution of 1-(bromomethyl)-4-nitrobenzene (10 g, 46.29 mmol) in acetone (15 mL) and the mixture stirred at rt for 2 h upon which a white precipitate formed. After completion of reaction (by TLC), the mixture was filtered and solid washed with EtOAc and acetone respectively to afford the desired product as off-white solid (12.0 g, 89%). 1H NMR (DMSO-d6): δ 9.17 (br s, 4H), 8.24 (d, J=8.40 Hz, 2H), 7.70 (d, J=8.40 Hz, 2H) and 4.66 (s, 2H). MS: 212.08 [M+H]+

Workup

  1. customformed
  2. customAfter completion of reaction (by TLC)
  3. filtrationthe mixture was filtered
  4. washsolid washed with EtOAc and acetone respectively

Sources & evidence

ORD record
ord-8c69260adb0145df90df8a80ef48cc7c
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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