Water → HCID 152773090, compound

HRID 1076043Notes

Reaction equation

HRID 1076043 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH3:8][O:9][C:10](=[NH:12])[NH2:11].O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>ClCCl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:23])[NH:12][C:10](=[NH:11])[O:9][CH3:8])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)

Product 1

HCID 152773090HCID 152773090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

320 Parts of a 50% sodium hydroxide solution was added dropwise to 345 parts of 2-methylpseudourea hydrogen sulfate in a mixture of 3500 parts of water and 4000 parts of dichloromethane which mixture was maintained at approximately 5°C. by a cooling bath. 307 Parts of p-chlorophenyl isocyanate was added to the resulting mixture and the cooling bath was removed. The reaction mas was stirred vigorously for 6 hours at room temperature. The dichloromethane layer was separated, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was triturated in hexane and the solid was collected by filtration affording 400 parts of methyl 4-(4-chlorophenyl)allophanimidate, m.p. 115°-117°C.

Workup

  1. customthe cooling bath was removed
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated in hexane
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-3e2231ff54864c0d9b310eb67bb78661
Source dataset
uspto-grants-1976_05
Patent number
US03954837

Reaction notes

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