Sulfuric Acid → [(2-methoxyphenyl)methyl]urea

HRID 2256019Notes

Reaction equation

HRID 2256019 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].S(=O)(=O)(O)O.[O-:16][C:17]#[N:18].[Na+]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:17]([NH2:18])=[O:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 812922-MethoxybenzylamineHCID 517096Sodium Cyanate

Product 1

HCID 1488713[(2-methoxyphenyl)methyl]ureaYield 94.3%

Conditions

Temperature
80 °C

Procedure

To an aqueous solution (13 ml) containing 2-methoxybenzylamine (13.7 g, 0.1 mol.) was added dropwise dilute sulfuric acid (prepared from 2.8 ml of conc. sulfuric acid and 6.7 ml of refined water) at room temperature. After completion of the dropwise addition, an aqueous solution (70 ml) containing sodium cyanate (7.65 g, 0.12 mol.) was added to the reaction mixture at room temperature taking 15 minutes. The suspension obtained as reaction mixture was heated at 80° C. for one hour. The reaction mixture was cooled, then resulting crystalline precipitates were collected by filtration, followed by recrystallization from ethanol to give 17 g (yield 94%) of colorless prisms.

Workup

  1. additionAfter completion of the dropwise addition
  2. additionwas added to the reaction mixture at room temperature
  3. customThe suspension obtained as reaction mixture
  4. temperatureThe reaction mixture was cooled
  5. customresulting crystalline precipitates
  6. filtrationwere collected by filtration
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-9d387aa9a9ca41e2b6614bf9b3704630
Source dataset
uspto-grants-1997_08
Patent number
US05654309

Reaction notes

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