Hydrochloric Acid → Ethyl 4-(trifluoromethyl)benzene-1-carboximidate hydrochloride

HRID 1386951Notes

Reaction equation

HRID 1386951 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH2:13]([OH:15])[CH3:14].[ClH:16]>C(Cl)(Cl)Cl>[ClH:16].[CH2:13]([O:15][C:7](=[NH:8])[C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:4][CH:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67995Benzonitrile, 4-(trifluoromethyl)-

Product 1

HCID 68765138Ethyl 4-(trifluoromethyl)benzene-1-carboximidate hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of 4-trifluoromethyl-benzonitrile (5.16 g, 30.2 mmol) and ethanol (1.39 ml, 30.2 mmol) in chloroform (15 ml) was saturated with a dry stream of HCl gas for 15 min. at −5° C. and the mixture allowed to stand 1 week at 4° C. The product was precipitated with ether, and the suspension stirred for 30 min. at −15°C., then filtered and washed with ether. The solid product was dried at r.t. under high vacuum overnight to afford the title compound (7.1 g, 28 mmol, 93% yield) as a white solid. MS: m/e=217 (M+), 172 (M+-EtOH)

Workup

  1. waitto stand 1 week at 4° C
  2. customThe product was precipitated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. customThe solid product was dried at r.t. under high vacuum overnight

Sources & evidence

ORD record
ord-7b3b0ce73772489aaab4a1dfbffeb6f5
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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