Hydrochloric Acid → 1-Methyl-1-(1,2,3,4-tetrahydro-1-naphthyl)urea

HRID 461376Notes

Reaction equation

HRID 461376 reaction equation
[CH3:1][NH:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.CO.Cl.[O-:16][C:17]#[N:18].[K+]>O>[CH3:1][N:2]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[C:17]([NH2:18])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 46475N-methyl-1,2,3,4-tetrahydronaphthalen-1-amineHCID 11378442Potassium cyanate

Product 1

HCID 213934931-Methyl-1-(1,2,3,4-tetrahydro-1-naphthyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 8.05 grams (0.05 mole) of 1,2,3,4-tetrahydro-N-methyl-1-naphthylamine in 10 ml. of methanol is added a solution of 4.2 ml. of 12N hydrochloric acid (0.05 mole) in 35 ml. of water. The mixture is cooled in an ice-water bath while a solution of 4.46 grams (0.055 mole) of potassium cyanate in 15 ml. is added dropwise. After the addition is complete, the reaction mixture is stirred at room temperature for 45 minutes and then at 70° to 75° C. for 30 minutes. The mixture is cooled to 25° C., and the solid product filtered off, washed with water and then with cold ethyl acetate. The dried product weights 7.1 grams and has melting point 160°-163° C. Recrystallization from acetone-hexane gives the analytical sample, melting point 161° C. to 163° C. Recrystallization from acetone-hexane gives the analytical sample, melting point 161° to 163° C. Analysis Calculated for C12H16N2O: C, 70.58; H, 7.90; N, 13.72. Found: C, 70.60; H, 7.94; N, 13.75.

Workup

  1. additionis added dropwise
  2. additionAfter the addition
  3. waitat 70° to 75° C. for 30 minutes
  4. temperatureThe mixture is cooled to 25° C.
  5. filtrationthe solid product filtered off
  6. washwashed with water
  7. customRecrystallization from acetone-hexane
  8. customgives the analytical sample, melting point 161° C. to 163° C
  9. customRecrystallization from acetone-hexane
  10. customgives the analytical sample, melting point 161° to 163° C

Sources & evidence

ORD record
ord-39ad0b0b826041bcb57fbe6f12314c72
Source dataset
uspto-grants-1977_12
Patent number
US04062856

Reaction notes

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