Triethylamine → HCID 79035731, compound

HRID 1429682Notes

Reaction equation

HRID 1429682 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:25][NH:26][O:27][CH3:28].CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:26]([O:27][CH3:28])[CH3:25])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3026202-Chloro-3-fluorobenzoic acid

Product 1

HCID 79035731HCID 79035731, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-3-fluorobenzoic acid (30 g, 172 mmol) in 300 mL of DCM was added carbonyldiimidazole (CDI) (32.0 g, 198 mmol) in portions. After addition and then stirring at RT for 1 h, N,O-dimethylhydroxylamine HCl salt (18.5 g, 189 mmol) was added into the mixture followed by Et3N (20 mL). The mixture was stirred at RT overnight. After the reaction was quenched with water, the aqueous layer was extracted with DCM (2×). The organic layers were washed with 2N HCl (aq), water, sat. NaHCO3 (aq) and brine. The solution was dried (MgSO4) and concentrated. The product 2-chloro-3-fluoro-N-methoxy-N-methylbenzamide (32.0 g) was obtained by silica gel chromatography (elution with 0-30% EtOAc/Hex).

Workup

  1. additionAfter addition
  2. stirringThe mixture was stirred at RT overnight
  3. customAfter the reaction was quenched with water
  4. extractionthe aqueous layer was extracted with DCM (2×)
  5. washThe organic layers were washed with 2N HCl (aq), water, sat. NaHCO3 (aq) and brine
  6. dry with materialThe solution was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0c6d2f09c6244c69afb9d1888c63603b
Source dataset
uspto-grants-2015_01
Patent number
US08940748B2

Reaction notes

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