Potassium Carbonate → HCID 20268380, compound

HRID 485613Notes

Reaction equation

HRID 485613 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH3:27])[CH2:12][O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]([O:23][C:24](Cl)=[O:25])[CH:20]=[CH:21][CH:22]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)C.O>[CH3:10][CH:11]([CH3:27])[CH2:12][O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]([O:23][C:24](=[O:25])[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:20]=[CH:21][CH:22]=1)=[O:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 702724-Chloro-N-methylbenzenamineHCID 53897145HCID 53897145, compound

Product 1

HCID 20268380HCID 20268380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 14.2 g (0.1 mole) 4-chloro-N-methylaniline in 100 ml acetic acid ethyl ester is mixed with 50 ml water. Then a solution of 27.2 g (0.1 mole) chloroformic acid-3-(2-methylpropoxycarbonylamino)-phenyl ester in 100 ml acetic acid ethyl ester and simultaneously a solution of 13.8 g (0.1 mole) potassium carbonate in 50 ml water is added in drops within 20 minutes while agitating and cooling to 10° to 15° C. Agitation is continued at 15° C. for another 30 minutes. Then the organic phase is separated, washing at 0° C. with dilute soda lye, dilute hydrochloric acid and water. Drying with magnesium sulfate is followed by evaporation under reduced pressure. Recrystallization from acetic acid ethyl ester/pentane.

Workup

  1. temperaturecooling to 10° to 15° C
  2. customThen the organic phase is separated
  3. washwashing at 0° C.
  4. additionwith dilute soda lye, dilute hydrochloric acid and water
  5. dry with materialDrying with magnesium sulfate
  6. customis followed by evaporation under reduced pressure
  7. customRecrystallization from acetic acid ethyl ester/pentane

Sources & evidence

ORD record
ord-b2137d77b814447892abb11800e86775
Source dataset
uspto-grants-1985_08
Patent number
US04537622

Reaction notes

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