1-Bromopropane → HCID 178460859, compound

HRID 260724Notes

Reaction equation

HRID 260724 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]([NH2:12])=[S:11].[CH2:13](Br)[CH2:14][CH3:15]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10](=[NH:12])[S:11][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 78401-BromopropaneHCID 22400378HCID 22400378, compound

Product 1

HCID 178460859HCID 178460859, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-chlorophenyl)methyl thiourea (3 g, 14.9 mmol) and propylbromide (13.5 g, 110 mmol) in acetonitrile (20 mL) was refluxed for 5 hours. The solvent was evaporated, the residue was dissolved in 200 mL of 50% water/ether and acidified with 48% hydrobromic acid solution. The two phases were separated, the aqueous layer was washed with ether and then the aqueous layer was basified with 10% sodium carbonate solution. The liberated product was extracted with diethyl ether, washed with water and brine, dried and concentrated to give 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea (2.82 g, 78%); mp 112°-114° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 200 mL of 50% water/ether
  4. customThe two phases were separated
  5. washthe aqueous layer was washed with ether
  6. extractionThe liberated product was extracted with diethyl ether
  7. washwashed with water and brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-629220f6940f4c29a1fb10c7dd7dc1b0
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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