4-Fluoroaniline → HCID 53654446, compound

HRID 1578937Notes

Reaction equation

HRID 1578937 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[N:12]=[C:11](Cl)[CH:10]=[C:9]([Cl:14])[N:8]=1)[CH3:2].[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[N:8]=[C:9]([Cl:14])[CH:10]=[C:11]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([F:16])=[CH:18][CH:19]=2)[N:12]=1)[CH3:2]

Participants

4

Reactant 3

HCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 4133103Acetic acid, [(4,6-dichloro-2-pyrimidinyl)thio]-, ethyl ester

Product 1

HCID 53654446HCID 53654446, compoundYield 30.3%

Procedure

A stirred mixture of 10.7 g of (4,6-dichloro-2-pyrimidinylthio)acetic acid ethyl ester, 4.4 g of p-fluoroaniline and 4.2 g of sodium carbonate was heated under reflux for 6 hr. and filtered. Water was added to the filtrate to the precipitation point. The precipitate was removed by filtration and recrystallized from 95% ethanol to afford 4.1 g of product; mp. 97°-102°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr
  3. filtrationand filtered
  4. additionWater was added to the filtrate to the precipitation point
  5. customThe precipitate was removed by filtration
  6. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-5c317d768f9543dabcfa10ade6a07564
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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