Water → HCID 178432777, compound

HRID 223361Notes

Reaction equation

HRID 223361 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([NH2:5])=[NH:4].C(=O)([O-])[O-].[K+].[K+].[Cl:14][CH:15]([C:21]([CH3:23])=O)[C:16](OCC)=[O:17].O>C1CCCCC1>[Cl:14][C:15]1[C:16]([OH:17])=[N:4][C:3]([C:2]([Cl:7])([Cl:6])[Cl:1])=[N:5][C:21]=1[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11858Ethyl 2-chloroacetoacetateHCID 356082,2,2-Trichloroethanimidamide

Product 1

HCID 178432777HCID 178432777, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture of 30.0 g (0.18 mole) trichloroacetamidine, 25.2 g (0.18 mole) potassium carbonate, 30.3 g (0.18 mole) ethyl 2-chloroacetoacetate, and 300 ml water was stirred 18 hours. The aqueous solution was decanted from heavier tars and acidified with hydrochloric acid. The precipitate that was formed was filtered, washed, and dried to give 14.7 g (31% yield; mp 130°-145° C.) of crude product. An analytical sample was prepared by recrystallization from cyclohexane (mp 156°-157° C.). The structure was confirmed via infrared and elemental analysis.

Workup

  1. customThe aqueous solution was decanted from heavier tars
  2. customThe precipitate that was formed
  3. filtrationwas filtered
  4. washwashed
  5. customdried
  6. customto give 14.7 g (31% yield; mp 130°-145° C.) of crude product

Sources & evidence

ORD record
ord-b6618cc3c5c9467f9aa1a89a32b8c6fc
Source dataset
uspto-grants-1982_10
Patent number
US04353908

Reaction notes

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