Thionyl Chloride → 4-(Morpholin-3-on-4-yl)-3-nitro-benzoic acid chloride

HRID 1629829Notes

Reaction equation

HRID 1629829 reaction equation
[C:1]([CH2:4][O:5][CH2:6][CH2:7][NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])(O)=[O:2].S(Cl)([Cl:23])=O>ClCCl.CN(C=O)C>[N:8]1([C:9]2[CH:17]=[CH:16][C:12]([C:13]([Cl:23])=[O:14])=[CH:11][C:10]=2[N+:18]([O-:20])=[O:19])[CH2:7][CH2:6][O:5][CH2:4][C:1]1=[O:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 667319084-(2-Carboxymethoxy-ethylamino)-3-nitro-benzoic acid

Product 1

HCID 860694074-(Morpholin-3-on-4-yl)-3-nitro-benzoic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

290 mg (1.02 mmol) 4-(2-carboxymethoxy-ethylamino)-3-nitro-benzoic acid in 100 ml dichloromethane are combined with 0.186 ml (2.55 mmol) thionyl chloride and 2 drops of DMF and refluxed for one day. After evaporation of the solution i. vac. it is evaporated with toluene and the residue is further reacted without any more purification.

Workup

  1. temperaturerefluxed for one day
  2. customAfter evaporation of the solution i
  3. customit is evaporated with toluene
  4. customthe residue is further reacted without any more purification

Sources & evidence

ORD record
ord-7fdb647b9f1c4c178508eef07b687bb0
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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