Hydrochloric Acid → HCID 53877200, compound

HRID 126764

Reaction equation

HRID 126764 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][C:12](=[N:15][C:16](=O)[O:17]C)[S:13][CH3:14].C[O-].[Na+].Cl>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[NH:15][CH:12]([S:13][CH3:14])[NH:11][C:9]2=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 693254-Methylphenyl isocyanateHCID 2935781-methoxycarbonyl-S-methylisothioureaHCID 10942334Sodium Methoxide

Product 1

HCID 53877200HCID 53877200, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylphenylisocyanate (19.0 g.) was added during 10 minutes to a solution of methyl N-[1-amino-1-(methylthio)methylene]carbamate (21.2 g.) in methylene chloride (200 ml.). After 2 hours of stirring, sodium methoxide [obtained by dissolving sodium (3.5 g.) in methanol (30 ml.)] was added at 15°-20° C. The subsequent mixture was stirred at that temperature for 18 hours and the resultant solid collected by filtration and dissolved in water (200 ml.). The solution obtained was acidified with concentrated hydrochloric acid and the solid which formed was collected by filtration, washed well with water and dried to give 3-(4-methylphenyl)-6-methylthiotetrahydro-1,3,5-triazine-2,4-dione (29 g., 81%), m.p. 276°-278° C.

Workup

  1. stirringThe subsequent mixture was stirred at that temperature for 18 hours
  2. filtrationthe resultant solid collected by filtration
  3. dissolutiondissolved in water (200 ml.)
  4. customThe solution obtained
  5. customthe solid which formed
  6. filtrationwas collected by filtration
  7. washwashed well with water
  8. customdried

Sources & evidence

ORD record
ord-08bda83688d34e06852d475c07644bc7
Source dataset
uspto-grants-1981_03
Patent number
US04254122

Linked notes

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