Hydrochloric Acid → HCID 18700301, compound

HRID 1604286Notes

Reaction equation

HRID 1604286 reaction equation
[C:1]([NH2:6])([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12](Cl)=[O:13].S(Cl)(Cl)=O.Cl>ClCCl>[C:1]([NH:6][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:9]([O:8][CH3:7])[CH:10]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 689862-Butanamine, 2-methyl-HCID 111276553-methoxy-4-nitro-benzoyl Chloride

Product 1

HCID 18700301HCID 18700301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

30 ml of tert-amylamine are added at 10° C. to a solution of 27 g of 3-methoxy-4-nitrobenzoyl chloride (obtained from 25 g of the corresponding acid and thionyl chloride at reflux for 4 hours, followed by evaporation under vacuum) in 250 ml of dichloromethane. The reaction mixture is stirred for 30 minutes at 20° C., 100 ml of a 1N hydrochloric acid solution are then added, the organic phase is separated by settling, washed and dried over MgSO4, the solvent is then evaporated and the residue is chromatographed on silica gel, elution being carried out with dichloromethane, to obtain 31 g of the expected product; M.p.=65° C.

Workup

  1. customthe organic phase is separated
  2. washwashed
  3. dry with materialdried over MgSO4
  4. customthe solvent is then evaporated
  5. customthe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-251583e30d7547419ab899e24b6788a4
Source dataset
uspto-grants-1999_11
Patent number
US05994350

Reaction notes

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