Thiourea → HCID 20456549, compound

HRID 904775Notes

Reaction equation

HRID 904775 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([Br:12])[CH3:11])([O-:3])=[O:2].[NH2:13][C:14]([NH2:16])=[S:15]>C(O)C>[BrH:12].[C:14]([S:15][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:11])(=[NH:13])[NH2:16]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 126434601-(1-Bromoethyl)-2-nitrobenzene

Product 1

HCID 20456549HCID 20456549, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 33.5 g of 1-(2-nitrophenyl)ethyl bromide and 11.4 g of thiourea in 375 ml absolute ethanol was stirred at reflux temperature for 31/2 hours. The reaction mixture was allowed to cool to room temperature and was concentrated to one-half volume in vacuo. The solution was then cooled to ca. -60° C. and 1-chlorobutane was added until a gummy solid formed. The supernatant was decanted and the residue dried in vacuo to give 38 g of 1-(2-nitrophenyl)ethyl carbamimidothioate hydrobromide as a light orange solid which was not further purified.

Workup

  1. temperatureat reflux temperature for 31/2 hours
  2. concentrationwas concentrated to one-half volume in vacuo
  3. temperatureThe solution was then cooled to ca. -60° C.
  4. addition1-chlorobutane was added until a gummy solid
  5. customformed
  6. customThe supernatant was decanted
  7. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-9f56934293f34c828195a38ba7428bed
Source dataset
uspto-grants-1983_12
Patent number
US04420325

Reaction notes

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