Dichloromethane → HCID 54115575, compound

HRID 1420149Notes

Reaction equation

HRID 1420149 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12][CH2:13][CH2:14][C:15](Cl)=[O:16].C(N(C(C)C)CC)(C)C.C(Cl)Cl>O>[N+:9]([C:4]1[CH:3]=[C:2]([F:1])[CH:8]=[CH:7][C:5]=1[NH:6][C:15](=[O:16])[CH2:14][CH2:13][Br:12])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 677694-Fluoro-2-nitroanilineHCID 81531DiisopropylethylamineHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 54115575HCID 54115575, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.8 gm of 4-fluoro-2-nitroaniline, 8.57 gm of 3-bromo propionylchloride (added at a temperature of 0° C. over a period of 0.3 hours), 6.5 gm of diisopropylethylamine and 150 ml CH2Cl2 was kept for 48 hours at 20-25° C. Water (300 ml) was added and the mixture was extracted with CH2C2. The CH2Cl2 extract was collected, washed with water (2×20 ml) and desiccated wtih Na2SO4. The crude product (14.7 gm) obtained after removal of solvents was used without further purification. A sample of this crude material (14.79 gm) exhibited the following data. M+/z of 292.

Workup

  1. extractionthe mixture was extracted with CH2C2
  2. extractionThe CH2Cl2 extract
  3. customwas collected
  4. washwashed with water (2×20 ml)

Sources & evidence

ORD record
ord-46c91d94587b4149a6923ad5c9665158
Source dataset
uspto-grants-1999_03
Patent number
US05889010

Reaction notes

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