Triethylamine → HCID 59774906, compound

HRID 2422513Notes

Reaction equation

HRID 2422513 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[N:2]1.Cl.[CH3:10][NH:11][O:12][CH3:13].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:13][O:12][N:11]([CH3:10])[C:6]([C:5]1[S:1][N:2]=[CH:3][CH:4]=1)=[O:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5200404Isothiazole-5-carboxylic acid

Product 1

HCID 59774906HCID 59774906, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-isothiazole carboxylic acid (5 g, 38.7 mmol) in dichloromethane (200 mL), 4-(dimethylamino)pyridine (473 mg, 3.87 mmol), N,O-dimethylhydroxylamine hydrochloride (4.53 g, 46.4 mmol) (N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (8.17 g, 42.6 mmol) and triethylamine (13.63 μL, 97.0 mmol) were added and the reaction was stirred overnight at room temperature. The reaction mixture was then successively washed with 1N HCl, 1N NaOH and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue obtained was used as such for the next step. 1H NMR (400 MHz, acetone-d6): 8.59 (s, 1H), 7.97 (s, 1H), 3.94 (s, 3H), 3.38 (s, 3H).

Workup

  1. washThe reaction mixture was then successively washed with 1N HCl, 1N NaOH and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b65d1e7206949c1b4a8dc1d08a943b0
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…