4-(Methylthio)aniline → N-[4-(Methylsulfanyl)phenyl]urea

HRID 1756690Notes

Reaction equation

HRID 1756690 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[O-:10][C:11]#[N:12].[Na+]>C(O)(=O)C.O>[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11]([NH2:12])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 660384-(Methylthio)anilineHCID 517096Sodium Cyanate

Product 1

HCID 306638N-[4-(Methylsulfanyl)phenyl]ureaYield 96.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 30 g (170 mmol) of 4-(methylmercapto)aniline dissolved in 83 ml of acetic acid and 165 ml of water was heated to 40° C. Once warmed to 40° C. a solution of sodium cyanate (22.2 g; 340 mmol) in 150 ml of water was slowly added. The resulting suspension was stirred for 15 minutes and then allowed to sit for 2 hours. Filtration of the suspension provided 29.98 g of title compound. m.p. 155°-159° C.

Workup

  1. additionwas slowly added
  2. waitto sit for 2 hours
  3. filtrationFiltration of the suspension

Sources & evidence

ORD record
ord-5a859bdb13594bed8f802d6f1328b913
Source dataset
uspto-grants-1995_08
Patent number
US05441984

Reaction notes

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