4-Fluoroaniline → HCID 13014494, compound

HRID 2198625Notes

Reaction equation

HRID 2198625 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([C:11](=[CH:20]OCC)[C:12]([NH:14][C:15](OCC)=[O:16])=[O:13])#[N:10]>C1C2C(=CC=CC=2)CCC1>[C:9]([C:11]1[C:12](=[O:13])[NH:14][C:15](=[O:16])[N:6]([C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)[CH:20]=1)#[N:10]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 13014494HCID 13014494, compound

Reagents, catalysts & solvents 1

HCID 8404TetralinSolvent

Procedure

Following the method of Example 2, 4-fluoroaniline (0.05 mol) is reacted with α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide (0.05 mol) and heated at reflux in tetralin to yield 5-cyano-1-(4-fluorophenyl)uracil, which is then reacted with trichloromethanesulfenyl chloride, in NaOH and dichloromethane, to yield the final product, 5-cyano-1-(4-fluorophenyl)-3-trichloromethanesulfenyluracil, m.p. 163°-165.5°.

Workup

  1. temperatureheated

Sources & evidence

ORD record
ord-ab66950cf138435b8af1f4b9defe8052
Source dataset
uspto-grants-1982_11
Patent number
US04358591

Reaction notes

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