Triethylamine → HCID 69916876, compound

HRID 2416509Notes

Reaction equation

HRID 2416509 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH:10]([O:20][CH3:21])[C:11]1[CH:19]=[CH:18][C:14](C(O)=O)=[CH:13][CH:12]=1.ClC([O:25][CH2:26]C)=O.[NH2:28][NH2:29]>ClCCl>[CH3:21][O:20][CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:18][C:19]=1[C:26]([NH:28][NH2:29])=[O:25])[O:9][CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 10928Ethyl chloroformateHCID 10888839HCID 10888839, compound

Product 1

HCID 69916876HCID 69916876, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

Triethylamine (11.8 mL, 84.6 mmol) was added to a solution of 4-(dimethoxymethyl)benzoic acid (11.0 g, 56.4 mmol, prepared as described in Tetrahedron 1998, 54,15679-15690) in dichloromethane (120 mL) at room temperature. The reaction mixture was cooled to −40° C., ethyl chloroformate (6.7 mL, 70.0 mmol) was added dropwise, and stirring continued at −40° C. for 30 min. Hydrazine (8.85 mL, 282 mmol) was added and the reaction mixture was warmed to room temperature and stirred for an additional 1 h. The reaction mixture was diluted with dichloromethane, washed with water, dried with Na2SO4, and concentrated in vacuo to give 9.06 g (77%) of the title compound, which was used in the next step without further purification. MS 211 (M+H)+.

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. stirringstirred for an additional 1 h
  3. washwashed with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8b8b29ab23245bc9823ec73bcde2c2e
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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