4-Methylmorpholine → HCID 86608958, compound

HRID 1710810Notes

Reaction equation

HRID 1710810 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:8]=1[C:9](O)=[O:10].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:8]=1[C:9]([N:3]([O:4][CH3:5])[CH3:2])=[O:10]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 6045422-Amino-3,6-dichlorobenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86608958HCID 86608958, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,O-dimethlyhydroxylamine hydrochloride (3.28 g, 33 mmol) and 2-amino-3,6-dichlorobenzoic acid (4.76 g, 22 mmol) were dissolved in DMF (110 ml). At r.t. under nitrogen and stirring, first N-methyl morpholine (10 g, 99 mmol) and then HBTU (12.5 g, 33 mmol) were added, and the reaction was stirred at r.t. overnight. The reaction was poured onto water and extracted twice with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was treated with heptane and little diethyl ether to yield 4 g of the product. The mother liquor was purified by column chromatography (silica gel, solvent gradient n-heptan/ethyl acetate=3/7) to give another batch of the title compound as an off-white solid (5.52 g, 100%).

Workup

  1. stirringthe reaction was stirred at r.t. overnight
  2. additionThe reaction was poured onto water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. additionThe residue was treated with heptane and little diethyl ether

Sources & evidence

ORD record
ord-dac7d6924e074f33a0c29e03ad40b47d
Source dataset
uspto-grants-2010_09
Patent number
US07790732B2

Reaction notes

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