Aniline → HCID 86756051, compound

HRID 1280590Notes

Reaction equation

HRID 1280590 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>C(#N)C>[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 80.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (15 g, 64.5 mmol) and aniline (12 mL, 132 mmol) in 200 mL of acetonitrile was stirred at room temperature for 24 hours. The mixture was then evaporated and ethyl acetate and 2M aqueous hydrochloric acid were added to the residue. The phases were separated and the organic phase was washed with aqueous hydrochloric acid, dried over sodium sulfate, filtered and evaporated. The resulting solid was purified by trituation with 1:3 ether/hexanes to give 14.2 g (64%) of ethyl 4-phenylamino-2-methylthio-pyrimidine-5-carboxylate as a white solid, mp 88.2-88.7° C.

Workup

  1. customThe mixture was then evaporated
  2. additionethyl acetate and 2M aqueous hydrochloric acid were added to the residue
  3. customThe phases were separated
  4. washthe organic phase was washed with aqueous hydrochloric acid
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was purified by trituation with 1:3 ether/hexanes

Sources & evidence

ORD record
ord-5e3ed3c7e9034301887b8c2fc352dff9
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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