Chloroform → HCID 20154698, compound

HRID 2413519Notes

Reaction equation

HRID 2413519 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[CH:7]=[N:8][CH:9]=[N:10][CH:11]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].C(Cl)(Cl)Cl>C(O)(=O)C.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH2:4][N:5]([C:6]1[CH:11]=[N:10][CH:9]=[N:8][CH:7]=1)[C:17](=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 20154703HCID 20154703, compound

Product 1

HCID 20154698HCID 20154698, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

2.80 g (11 mmol) of N-(2,4-dichlorobenzyl)-N-(pyrimidin-5-yl)amine are dissolved in 5 ml of glacial acetic acid and then 5 ml of acetic anhydride and 3 drops of concentrated sulfuric acid are added to the solution. With stirring, the reaction mixture is boiled under reflux for 11/2 hours and subsequently cooled. 30 ml of chloroform are added to the mixture, the acetic acid is removed by extraction with water and the separated solution of chloroform is dried over sodium sulfate. The sodium sulfate is filtered off and the chloroform is then evaporated off in vacuo at 80° C. and the residue is recrystallised from a mixture of 5 ml of toluene and 5 ml of cyclohexane, affording 2.23 g (68.5% of theory) of N-(2,4-dichlorobenzyl)-N-(pyrimidin-5-yl)acetamide, m.p. 134°-136° C. A further 0.90 g (27.6% of theory) of pure product is obtained by purifying the product formed in the filtrate through a column of silica gel (eluant: ethyl acetate).

Workup

  1. temperatureunder reflux for 11/2 hours
  2. temperaturesubsequently cooled
  3. customthe acetic acid is removed by extraction with water
  4. dry with materialthe separated solution of chloroform is dried over sodium sulfate
  5. filtrationThe sodium sulfate is filtered off
  6. customthe chloroform is then evaporated off in vacuo at 80° C.
  7. customthe residue is recrystallised from a mixture of 5 ml of toluene and 5 ml of cyclohexane

Sources & evidence

ORD record
ord-37460c006aa54f0daa84fef2a5c38629
Source dataset
uspto-grants-1988_01
Patent number
US04718934

Reaction notes

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