Sodium Carbonate → HCID 21319728, compound

HRID 262020Notes

Reaction equation

HRID 262020 reaction equation
[K].[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[OH:9].[CH3:16][C:17]([O:21][CH:22](Cl)[CH3:23])([CH3:20])[C:18]#[CH:19].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:15])[N:12]([CH3:13])[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH:22]([O:21][C:17]([CH3:20])([CH3:16])[C:18]#[CH:19])[CH3:23]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 182205N'-(3-Chloro-4-hydroxyphenyl)-N,N-dimethylcarbamimidic acidHCID 5462222PotassiumHCID 21319727HCID 21319727, compound

Product 1

HCID 21319728HCID 21319728, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a well-stirred suspension of the potassium salt of 3-chloro-4-hydroxyphenyl-1,1-dimethylurea (0.04 mole) in dry acetone (150 ml.) is added dropwise 1-chloroethyl 1,1-dimethyl-2-propynyl ether (5.9 grams, 0.04 mole). During the addition, an exotherm to 35° C. is observed; the reaction is stirred at room temperature overnight, then poured into an aqueous 10% sodium carbonate solution containing 200 grams of ice, and the mixture stirred vigorously for 30 minutes. The resulting solid is filtered off, water-washed and dried to give 8.5 grams, melting point 99° C. to 101° C., crystallization from hexane-cyclohexane-benzene gave 4.69 grams (36%), melting point 101° C. to 103° C.

Workup

  1. additionDuring the addition
  2. customto 35° C.
  3. stirringthe mixture stirred vigorously for 30 minutes
  4. filtrationThe resulting solid is filtered off
  5. washwater-washed
  6. customdried
  7. customto give
  8. custom8.5 grams, melting point 99° C. to 101° C., crystallization from hexane-cyclohexane-benzene
  9. customgave 4.69 grams (36%), melting point 101° C. to 103° C.

Sources & evidence

ORD record
ord-6cd4616aace242a0b52a9c7458e3528f
Source dataset
uspto-grants-1979_05
Patent number
US04153448

Reaction notes

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