Triethylamine → HCID 23042125, compound

HRID 2166088Notes

Reaction equation

HRID 2166088 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[C:10]([NH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21])=[O:11].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[C:10]([NH:12][N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:21])([F:22])[F:23])[C:2]([O:4][CH2:5][CH3:6])=[O:3])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 23042108HCID 23042108, compound

Product 1

HCID 23042125HCID 23042125, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.8 ml (19 mmol) of ethyl chloroformate are added dropwise while cooling to a mixture of 4.28 g (14 mmol) of 2-chloro-N'-(α,α,α-trifluoro-o-tolyl)-benzhydrazide and 2.7 ml (19 mmol) of triethylamine in 30 ml of toluene. The reaction mixture is heated at the reflux temperature for a further 4 hours and then extracted with diethyl ether against water and sodium bicarbonate solution. The organic phase is dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residual oil is then purified by chromatography using ethyl acetate/n-hexane (1:4) as the eluent. In this manner there is obtained ethyl 3-(2-chlorobenzoyl)-2-(α,α,α-trifluoro-o-tolyl)-carbazate as an almost colourless oil, IR spectrum (CHCl3): 3405, 1735, 1710 cm-1 ; 1H-NMR (CDCl3): 4.28 (q,OCH2CH3).

Workup

  1. temperatureThe reaction mixture is heated at the reflux temperature for a further 4 hours
  2. extractionextracted with diethyl ether against water and sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residual oil is then purified by chromatography

Sources & evidence

ORD record
ord-0def1178ef2e4debb7b698a3c614682f
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

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