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

HRID 2094259

Reaction equation

HRID 2094259 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-cc7afd95aa38442e8bcc227179813f27
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Linked notes

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