4-Chloroaniline → HCID 54239081, compound

HRID 1578936Notes

Reaction equation

HRID 1578936 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].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[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]([Cl:16])=[CH:18][CH:19]=2)[N:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 10340Sodium CarbonateHCID 4133103Acetic acid, [(4,6-dichloro-2-pyrimidinyl)thio]-, ethyl ester

Product 1

HCID 54239081HCID 54239081, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 8.0 g of (4,6-dichloro-2-pyrimidinylthio)acetic acid ethyl ester, 3.8 g of p-chloroaniline and 3.2 g of sodium carbonate in 100 ml. of ethanol was heated under reflux for 5 hr. The reaction mixture was filtered and water was added to the filtrate until precipitation resulted. Recrystallization of this material from 95% ethanol afforded 3.0 g of product, mp. 109°-112°C.

Workup

  1. temperatureunder reflux for 5 hr
  2. filtrationThe reaction mixture was filtered
  3. additionwater was added to the filtrate until precipitation
  4. customresulted
  5. customRecrystallization of this material from 95% ethanol

Sources & evidence

ORD record
ord-a9850172b8494f649dd21fd2157bc5a6
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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