Dichloromethane → HCID 13233176, compound

HRID 1605840Notes

Reaction equation

HRID 1605840 reaction equation
[NH2:1][C:2](=[N:5][C:6](=[O:9])OC)[S:3][CH3:4].C(Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1.C[O-].[Na+]>CCOCC.CO>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:21](=[O:22])[N:1]=[C:2]([S:3][CH3:4])[NH:5][C:6]2=[O:9])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 76934-Chlorophenyl IsocyanateHCID 2935781-methoxycarbonyl-S-methylisothioureaHCID 10942334Sodium Methoxide

Product 1

HCID 13233176HCID 13233176, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 148 parts of methyl N-(1-amino-1-methylthiomethylene)-carbamate, prepared as in Example 2, in 2,000 parts methylene chloride is added 154 parts of p-chlorophenyl isocyanate. The reaction is stirred for 3 days. Then to it is added 54 parts of sodium methoxide in 540 parts of methanol. The reaction mixture is then refluxed for 1 hour. The reaction mass is cooled, and 2,000 parts of ether are added. The solid collected by filtration is dissolved in water and the solution neutralized with hydrochloric acid. The new solid thus formed is collected, dried, and recrystallized from ethanol/H2O to give 140 parts of 3-(p-chlorophenyl)-6-methylthio-s-triazine-2,4(1H,3H)-dione melting at 292°-295°C.

Workup

  1. temperatureThe reaction mixture is then refluxed for 1 hour
  2. temperatureThe reaction mass is cooled
  3. filtrationThe solid collected by filtration
  4. dissolutionis dissolved in water
  5. customThe new solid thus formed
  6. customis collected
  7. customdried
  8. customrecrystallized from ethanol/H2O

Sources & evidence

ORD record
ord-95cbf02f70e7489c9c59dc4e850532e6
Source dataset
uspto-grants-1976_04
Patent number
US03951971

Reaction notes

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