Sodium Carbonate → HCID 21319731, compound

HRID 262019Notes

Reaction equation

HRID 262019 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:17])[N:14](C)C)[CH:8]=[CH:9][C:10]=1[OH:11].[Na].[CH3:19][C:20]([O:24][CH2:25]Cl)([CH3:23])[C:21]#[CH:22].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O>[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:17])[NH2:14])[CH:8]=[CH:9][C:10]=1[O:11][CH2:25][O:24][C:20]([CH3:23])([CH3:19])[C:21]#[CH:22]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 182205N'-(3-Chloro-4-hydroxyphenyl)-N,N-dimethylcarbamimidic acidHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 13694639HCID 13694639, compound

Product 1

HCID 21319731HCID 21319731, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Sodium methoxide (0.54 gram, 0.01 mole) is added to a methanolic solution of 3-(3-chloro-4-hydroxyphenyl)-1,1-dimethylurea (2.14 grams, 0.01 mole) and the mixture heated at reflux during 2 hours. The solvent is removed under reduced pressure and to the residual material dry benzene is added and evaporated off. This procedure is repeated until a dry white powder is obtained. The sodium salt is suspended in dry acetone (50 ml.) and chloromethyl 1,1-dimethyl-2-propynyl ether (1.45 grams, 0.011 mole) is added dropwise with stirring. After the initial exothermic reaction the reaction mixture is allowed to stir for a further 4.5 hours, then cold aqueous sodium carbonate solution (10% w/v, 100 ml.) followed by water (50 ml.) are added(1) and stirred. The resulting solid(2) is filtered off, water washed and air dried. Crystallization from benzene-hexane affords 2.2 grams, 70%; melting point 150° C. to 151° C. of Compound 1.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux during 2 hours
  3. customThe solvent is removed under reduced pressure and to the residual material dry benzene
  4. additionis added
  5. customevaporated off
  6. customis obtained
  7. customAfter the initial exothermic reaction the reaction mixture
  8. stirringto stir for a further 4.5 hours
  9. stirringstirred
  10. filtrationThe resulting solid(2) is filtered off
  11. washwater washed
  12. customair dried
  13. customCrystallization from benzene-hexane
  14. customaffords 2.2 grams, 70%

Sources & evidence

ORD record
ord-7c66580e57a9456f812ad01eefb13dcc
Source dataset
uspto-grants-1979_05
Patent number
US04153448

Reaction notes

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