4-Methylmorpholine → HCID 86608958, compound

HRID 505334Notes

Reaction equation

HRID 505334 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 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,O-dimethylhydroxylamine hydrochloride (3.28 g, 33 mmol) and 2-amino-3,6-dichlorobenzoic acid (4.76 g, 22 mmol) were dissolved in DMF (110 ml). N-methylmorpholine (9.99 g, 99 mmol) and HBTU (12.5 g, 33 mmol) were added and the reaction was stirred over night (r.t.). The reaction was poured onto water, extracted twice with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated. The residue was crystallized with heptane and a little bit of diethyl ether. The filtrate was purified by column chromatography (heptane:ethyl acetate=1:1) to yield the product as an off-white solid (5.52 g, 100%).

Workup

  1. additionThe reaction was poured onto water
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was crystallized with heptane
  7. customThe filtrate was purified by column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2d531e64583c48938fab372965d049b6
Source dataset
uspto-grants-2010_08
Patent number
US07781441B2

Reaction notes

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