Triethylamine → HCID 54558707, compound

HRID 581914Notes

Reaction equation

HRID 581914 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(N(CC)CC)C.[I:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>CN(C=O)C>[I:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122713-IodoanilineHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 54558707HCID 54558707, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-3-nitrobenzonitril (1.82 g, 10 mmol) in dry DMF (25 ml) is added triethylamine (1.54 ml, 11 mmol) and 3-iodoaniline (1.2 ml, 10 mmol) and the mixture is heated to 80-100° C. over night. After cooling the mixture is poured into four volumes of ice-water. The precipitate is filtered off, washed with water and dried. This crude product is washed with hot ethanol to yield 2.1 g (58%) of the title compound. Mp. 211-212° C.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customdried
  5. washThis crude product is washed with hot ethanol

Sources & evidence

ORD record
ord-3d287082a135436a801df3af7b70d7eb
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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