Triethylamine → 2,2,2-Trifluoroethoxybenzamide

HRID 1973189Notes

Reaction equation

HRID 1973189 reaction equation
C1[NH:3]C1.C(N(CC)CC)C.[F:11][C:12]([F:31])([F:30])[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:21](OCC(F)(F)F)=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C(OCC)C>[F:11][C:12]([F:31])([F:30])[CH2:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH2:3])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9033AziridineHCID 11427683Benzoyl chloride, 2,5-bis(2,2,2-trifluoroethoxy)-

Product 1

HCID 190095772,2,2-Trifluoroethoxybenzamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyleneimine (2.9 g., 0.068 mole), triethylamine (6.8 g., 0.068 mole) and diethyl ether (250 ml.) are cooled to 0° C. and stirred while adding 2,5-di-(2,2,2-trifluoroethoxy)benzoyl chloride (22.8 g., 0.068 mole). The mixture is allowed to warm to room temperature and filtered. The filtrate is treated with 6.6 N isopropanol-hydrochloric acid mixture and filtered and the solvent evaporated in vacuo to give N-(2-chloroethyl)-2,5-di-(2,2,2-trifluoroethoxy-benzamide, m.p. 87°-88.5° C.

Workup

  1. filtrationfiltered
  2. additionThe filtrate is treated with 6.6 N isopropanol-hydrochloric acid mixture
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-7238b696e790457e8c5b169556d7a4e0
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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