Triethylamine → 4-Amino-5-chloro-N,2-dimethoxy-N-methylbenzamide

HRID 963336Notes

Reaction equation

HRID 963336 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.Cl.[CH3:34][NH:35][O:36][CH3:37]>CN(C=O)C.O>[CH3:37][O:36][N:35]([CH3:34])[C:6](=[O:8])[C:5]1[CH:9]=[C:10]([Cl:11])[C:2]([NH2:1])=[CH:3][C:4]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 816264-Amino-5-chloro-2-methoxybenzoic acid

Product 1

HCID 190818494-Amino-5-chloro-N,2-dimethoxy-N-methylbenzamideYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Amino-5-chloro-2-methoxybenzoic acid (10.1 g, 50 mmol) was dissolved in DMF (50 mL). Carbonyldiimidazole (8.9 g, 55 mmol) was added to the solution and the mixture was stirred for 15 minutes. Triethylamine (7 mL, 5.1 g, 50 mmol) and N,O-dimethylhydroxylamine hydrochloride (6.3 g, 65 mmol) were added and the mixture was stirred for 12 hours. The mixture was then diluted with water and extracted into ethyl acetate. The ethyl acetate extract was washed with 5% HCl, with water, and then with brine. The extract was dried over sodium sulfate and then evaporated. Crystallization from ethyl acetate gave N-methoxy-N-methyl-4-amino-5-chloro-2-methoxybenzamide (10 g, 41 mmol), m.p. 134°-135° C.

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractionextracted into ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with 5% HCl, with water
  5. dry with materialThe extract was dried over sodium sulfate
  6. customevaporated
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-c372688583df4b249a171ef2e712d810
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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