Ammonia → 3-Amino-2,4-dichlorobenzamide

HRID 450325Notes

Reaction equation

HRID 450325 reaction equation
ClC([N:6](C)C)=C(C)C.[NH2:9][C:10]1[C:11]([Cl:20])=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:13](O)=[O:14].N>C1COCC1>[NH2:9][C:10]1[C:11]([Cl:20])=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:13]([NH2:6])=[O:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 152782343-Amino-2,4-dichlorobenzoic acid

Product 1

HCID 586254673-Amino-2,4-dichlorobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1-Chloro-2-methyl-propenyl)-dimethyl-amine (16.1 mL, 116 mmol) is added to 3-amino-2,4-dichloro-benzoic acid (20.0 g, 97.1 mmol) in THF (320 mL). After 4 h at rt the mixture is added dropwise to conc. NH3 (320 mL) and stirred at rt overnight. The reaction mixture is concentrated, cooled and filtered. The filtercake is dried to give the sub-title compound.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtercake is dried

Sources & evidence

ORD record
ord-7f7ea0ced36c456d9beaf1e96b19dcc9
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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