Aniline → HCID 86756051, compound

HRID 1858193Notes

Reaction equation

HRID 1858193 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1>[C:15]1([NH:14][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86756051HCID 86756051, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4 g (17.2 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate and 5 g (54 mmol) of aniline in 40 ml of dioxan was stirred at room temperature for 24 hours. The mixture was then evaporated and 100 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid were added to the residue. The phases were separated and the organic phase was washed with 50 ml of aqueous hydrochloric acid, dried over magnesium sulfate, filtered and evaporated. The resulting solid was purified by crystallisation from aqueous ethanol to give 3.5 g (64%) of ethyl 4-phenylamino-2-methylthiopyrimidine-5-carboxylate as a white solid.

Workup

  1. customThe mixture was then evaporated
  2. addition100 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid were added to the residue
  3. customThe phases were separated
  4. washthe organic phase was washed with 50 ml of aqueous hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was purified by crystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-b20ce59d09ce406281113aea052e865c
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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