Ammonia → 3-Amino-2-chlorobenzamide

HRID 1508168Notes

Reaction equation

HRID 1508168 reaction equation
[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].CC[N:14](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.N>C(Cl)Cl.O.CCOC(C)=O>[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:14])=[O:6]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4593153-Amino-2-chlorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 544096263-Amino-2-chlorobenzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-2-chlorobenzoic acid (5.8 mmol) in 12 mL DCM were added 3.0 mL DIPEA, HOBT (7.0 mmol) and EDC.HCl (7.0 mmol) followed by the addition of 0.67 mL of a solution of NH3 in water (13M). The mixture was stirred at RT overnight, EtOAc was then added and the mixture was extracted with water, sat. aq. NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to obtain the desired compound as yellow solid.

Workup

  1. extractionthe mixture was extracted with water, sat. aq. NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94310c0c15f946ef87d7511c86cc4499
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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