Water → HCID 25110856, compound

HRID 751543Notes

Reaction equation

HRID 751543 reaction equation
F[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[CH2:13][CH2:14][O:15][C:16](Cl)=[O:17].[CH3:19][O-:20].[Na+].O>CN1CCCC1=O>[CH3:19][O:20][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:13][CH2:14][O:15][C:16]2=[O:17])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 123052-Chloroethyl chloroformateHCID 677684-Fluoro-3-nitroanilineHCID 10942334Sodium Methoxide

Product 1

HCID 25110856HCID 25110856, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Fluoro-3-nitro-aniline (50.0 g) is dissolved in 100 ml N-methyl-pyrrolidone. Subsequently 2-chloroethyl-chloroformate (48.1 g) is added dropwise under external cooling, whereupon the internal temperature is kept below 60° C. After completion of the addition stirring is continued for 30 minutes and then a 30% methanolic sodium methoxide solution (230.7 g) is added dropwise in such a rate that under external cooling the temperature remains below 40° C. When the addition is completed, the reaction mixture is allowed to cool and then poured into cold water (2000 ml) and stirred for additional 30 minutes. The obtained suspension is filtered off, washed with water, and dried.

Workup

  1. customis kept below 60° C
  2. additionAfter completion of the addition
  3. temperatureunder external cooling the temperature
  4. customremains below 40° C
  5. additionWhen the addition
  6. temperatureto cool
  7. stirringstirred for additional 30 minutes
  8. filtrationThe obtained suspension is filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-2d1a79f5acb748b5acb519668313ef0e
Source dataset
uspto-grants-2008_07
Patent number
US07405325B2

Reaction notes

Loading…