1-Butanol → HCID 14391422, compound

HRID 1638241Notes

Reaction equation

HRID 1638241 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[NH:21][C:22]([C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][C:30](Cl)=[O:31])=[CH:26][CH:25]=1)=[O:23].Cl>O1CCOCC1>[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[NH:21][C:22]([C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][C:30]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:31])=[CH:26][CH:25]=1)=[O:23]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14391421HCID 14391421, compound

Product 1

HCID 14391422HCID 14391422, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

On the other hand, 0.8 g of n-butanol and 2.0 g of triethylamine were dissolved in 20 ml of dioxane. To this solution, a solution prepared by dissolving above 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetyl chloride in 5 ml of dioxane, was dropwise added over a period of 5 minutes at room temperature under stirring. After completion of the dropwise addition, the stirring was continued at room temperature for further 5 hours. After completion of the reaction, the reaction solution was poured into 200 ml of a 2% hydrochloric acid aqueous solution. The precipitates were collected by filtration, washed with a dilute alkaline aqueous solution and water, and dried. Then, the precipitates were recrystallized from toluene to obtain 3.3 g of n-butyl 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetate. Yield: 80.5% as calculated on the basis of 4-(2,3-dichlorophenyl)carbamoylacetic acid) Melting point: 132°-136° C.

Workup

  1. customTo this solution, a solution prepared
  2. additionwas dropwise added over a period of 5 minutes at room temperature
  3. additionAfter completion of the dropwise addition
  4. customAfter completion of the reaction
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with a dilute alkaline aqueous solution and water
  7. customdried
  8. customThen, the precipitates were recrystallized from toluene

Sources & evidence

ORD record
ord-93d0055b96d34beb9ecbfac04d1cff39
Source dataset
uspto-grants-1989_11
Patent number
US04878942

Reaction notes

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