Triethylamine → HCID 57450911, compound

HRID 1691902Notes

Reaction equation

HRID 1691902 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8](C(O)=O)[CH2:7][CH2:6]1)=[O:4].C([N:16]([CH2:19]C)CC)C.ClC(OCC)=[O:23]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([C:19](=[O:23])[NH2:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

Product 1

HCID 57450911HCID 57450911, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture cyclohexane-1,4-dicarboxylic acid monomethyl ester (3 g, 16.1 mmol) and triethylamine (2.24 mL, 16.1 mmol) in chloroform cooled in an icebath was dripped in of ethyl chloroformate (1.54 g, 16.1 mmol) followed by bubbling of ammonia gas for 15 min. The reaction was stirred for 1 hr, filtered, the precipitate washed with chloroform, the filtrate diluted with dichloromethane (500 mL) and washed with aqueous sodium bicarbonate (saturated, 500 mL) and brine (250 mL), dried over sodium sulfate, and concentrated to give carbamoyl-cyclohexanecarboxylic acid methyl ester (2.1 g, 72%) as a white solid. LCMS calcd for C9H15NO3 (m/e) 185, obsd 186 (M+H).

Workup

  1. customby bubbling of ammonia gas for 15 min
  2. filtrationfiltered
  3. washthe precipitate washed with chloroform
  4. additionthe filtrate diluted with dichloromethane (500 mL)
  5. washwashed with aqueous sodium bicarbonate (saturated, 500 mL) and brine (250 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3b88ea2c6faa4cb3adacc921a68c6342
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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