1,1'-Carbonyldiimidazole → N-methoxy-N-methyloxane-4-carboxamide

HRID 2088911Notes

Reaction equation

HRID 2088911 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[O:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]1.Cl.[CH3:23][NH:24][O:25][CH3:26]>ClCCl>[CH3:26][O:25][N:24]([CH3:23])[C:19]([CH:16]1[CH2:15][CH2:14][O:13][CH2:18][CH2:17]1)=[O:21]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 219302Oxane-4-carboxylic acid

Product 1

HCID 23144693N-methoxy-N-methyloxane-4-carboxamideYield 114.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 1,1′-carbonyldiimidazole (333.41 g, 1.2 eq) to a solution of tetrahydro-2H-pyran-4-carboxylic acid (223 g, 1.71 mol) in dichloromethane (2.23 L) portion wise over 15 minutes. Stir for two hours. Add N,O-dimethylhydroxylamine hydrochloride (183.86 g, 1.1 eq) portionwise and stir for three hours. Wash the organics with saturated aqueous ammonium chloride, then with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give N-methoxy-N-methyl-tetrahydropyran-4-carboxamide (339 g, 114%) as crude material and use as such in next reaction. 1H NMR (300 MHz, DMSO-d6) δ 4.02 (m, 2H), 3.71 (s, 3H), 3.46 (m, 2H), 3.19 (s, 3H), 2.91 (m, 1H), 1.86 (m, 2H), 1.65 (m, 2H).

Workup

  1. washWash the organics with saturated aqueous ammonium chloride
  2. dry with materialDry the organics over anhydrous magnesium sulfate
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d26f44a800734becad068cc96521c242
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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