Aniline → HCID 54555807, compound

HRID 1578935Notes

Reaction equation

HRID 1578935 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9](Cl)[N:8]=1)[CH3:2].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[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]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=[C:11]([Cl:13])[N:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 4133103Acetic acid, [(4,6-dichloro-2-pyrimidinyl)thio]-, ethyl ester

Product 1

HCID 54555807HCID 54555807, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 8.0 g of (4.6-dichloro-2-pyrimidinylthio)acetic acid ethyl ester, 2.8 g of aniline 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 to start precipitation. The crude product was recrystallized from 95% ethanol to afford 6.7 g of product, mp. 109°-114°C.

Workup

  1. temperatureunder reflux for 5 hr
  2. filtrationThe reaction mixture was filtered
  3. additionwater was added to the filtrate
  4. customprecipitation
  5. customThe crude product was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-7b4687c9dfd545fea458d2a8e8e6e301
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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