Triethylamine → 2-Chloro-N-methoxy-N,3-dimethylbenzamide

HRID 419139

Reaction equation

HRID 419139 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:12][NH:13][O:14][CH3:15].CCN(CC)CC.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:13]([O:14][CH3:15])[CH3:12])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 111923Propylphosphonic anhydrideHCID 1398792-Chloro-3-methylbenzoic acid

Product 1

HCID 539138242-Chloro-N-methoxy-N,3-dimethylbenzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled mixture of 2-chloro-3-methyl-benzoic acid (1 g, 5.88 mmol), N,O-dimethylhydroxylamine (860 mg, 8.82 mmol) and Et3N (3.27 mL, 23.52 mmol) in CH2Cl2 (10 mL) was added 1-propane phosphonic acid cyclic anhydride (4.49 mL, 7.05 mmol; 50 wt % solution in EtOAc) dropwise and stirred at room temperature for 3 h. The reaction mixture was filtered, washed with CH2Cl2 (2×10 mL), evaporated to dryness and subjected to column chromatography (SiO2, 40% EtOAc-hexanes) to obtain 2-chloro-N-methoxy-3,N-dimethyl-benzamide (1.19 g) in 95% yield. ESMS m/z (relative intensity): 214 (M+H)+ (100).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with CH2Cl2 (2×10 mL)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-42b122a0adcf46068ab78e4f3391f2ba
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Linked notes

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