Triethylamine → HCID 70452962, compound

HRID 1732039Notes

Reaction equation

HRID 1732039 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15].ClC(OCC)=O.[NH2:28][CH:29]1[CH2:33][N:32]([CH2:34][CH3:35])[N:31]([CH2:36][CH3:37])[CH2:30]1>C(Cl)Cl>[OH2:15].[Br:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([NH:28][CH:29]1[CH2:33][N:32]([CH2:34][CH3:35])[N:31]([CH2:36][CH3:37])[CH2:30]1)=[O:16].[Br:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([NH:28][CH:29]1[CH2:33][N:32]([CH2:34][CH3:35])[N:31]([CH2:36][CH3:37])[CH2:30]1)=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 5591991,2-Diethyl-4-pyrazolidinamineHCID 135050975-Bromo-2,4-dimethoxybenzoic acid

Product 1

HCID 70452962HCID 70452962, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of triethylamine (1.52 g, 0.0150 mole) in 5 ml methylene chloride was added to a stirred solution of 5-bromo-2,4-dimethoxybenzoic acid (3.92 g, 0.0150 mole) in 75 ml of methylene chloride. After stirring for 20 minutes at room temperature, the mixture was cooled to 0° C. with an ice water bath. A solution of ethyl chloroformate (1.63 g, 0.0150 mole) in 10 ml methylene chloride was added dropwise to the cold stirred reaction mixture, and the mixture stirred at 0° C. for 30 minutes. Then a solution of 4-amino-1,2-diethylpyrazolidine (2.15 g, 0.0150 mole) in 10 ml of methylene chloride was added dropwise to the cold reaction mixture. The mixture was stirred for 30 minutes at 0° C. and then allowed to warm to room temperature and stirred for 16 hr. The mixture was concentrated to a semi-solid residue which was triturated in 10 ml methanol and 20 ml of a saturated aqueous sodium bicarbonate solution. The mixture was extracted with 2×75 ml portions of methylene chloride, the extract dried (magnesium sulfate) and concentrated to give a solid. The solid was triturated with isopropyl ether and filtered to give 4.28 g (73.9%) of cream-colored solid; recrystallization from isopropyl ether gave 2.04 g of the product; m.p. 113.5°-114.5° C. NMR analysis showed the solid to be a monohydrate, vacuum drying at 54° C. for 16 hrs gave the hemihydrate, m.p. 114°-115° C.

Workup

  1. temperaturethe mixture was cooled to 0° C. with an ice water bath
  2. stirringstirred
  3. customreaction mixture
  4. stirringthe mixture stirred at 0° C. for 30 minutes
  5. stirringThe mixture was stirred for 30 minutes at 0° C.
  6. temperatureto warm to room temperature
  7. stirringstirred for 16 hr
  8. concentrationThe mixture was concentrated to a semi-solid residue which
  9. customwas triturated in 10 ml methanol
  10. extractionThe mixture was extracted with 2×75 ml portions of methylene chloride
  11. dry with materialthe extract dried (magnesium sulfate)
  12. concentrationconcentrated
  13. customto give a solid
  14. customThe solid was triturated with isopropyl ether
  15. filtrationfiltered

Sources & evidence

ORD record
ord-cec2991d7cde45909a812452daefbfe7
Source dataset
uspto-grants-1986_11
Patent number
US04624961

Reaction notes

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