Triethylamine → HCID 58137436, compound

HRID 1258509Notes

Reaction equation

HRID 1258509 reaction equation
[NH2:1][C:2]1[C:3]([S:12]([F:17])([F:16])([F:15])([F:14])[F:13])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([S:12]([F:14])([F:15])([F:16])([F:17])[F:13])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([N:20]([O:21][CH3:22])[CH3:19])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 57943993HCID 57943993, compound

Product 1

HCID 58137436HCID 58137436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-methyl-4-(pentafluorosulfanyl)benzoic acid (500 mg, WO 2005/47239) was dissolved in methylene chloride (30 ml) and admixed while stirring with N,O-dimethylhydroxylamine hydrochloride (176 mg), 1-propanephosphonic anhydride (1.1 ml) and triethylamine (0.25 ml). After stirring for 4 h and leaving to stand overnight, the reaction mixture was concentrated, the residue was taken up with ethyl acetate and the solution was washed twice with potassium hydrogen sulfate solution and twice with sodium hydrogencarbonate solution. After drying over magnesium sulfate, the organic phase was filtered and concentrated. The resulting crude product (500 mg) was converted further directly.

Workup

  1. customleaving
  2. waitto stand overnight
  3. concentrationthe reaction mixture was concentrated
  4. washthe solution was washed twice with potassium hydrogen sulfate solution and twice with sodium hydrogencarbonate solution
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationthe organic phase was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-532dcba4d0f84bf19d01c07b40f804e5
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

Loading…