Diisopropylethylamine → 3-Chloro-N'-hydroxy-4-(trifluoromethoxy)benzimidamide

HRID 57389Notes

Reaction equation

HRID 57389 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])[C:5]#[N:6].Cl.[NH2:16][OH:17].C(N(C(C)C)C(C)C)C>C(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:12])([F:13])[F:14])/[C:5](=[N:16]/[OH:17])/[NH2:6]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 27738463-chloro-4-(trifluoromethoxy)benzonitrile

Product 1

HCID 585387863-Chloro-N'-hydroxy-4-(trifluoromethoxy)benzimidamideYield 62.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-chloro-4-(trifluoromethoxy)benzonitrile (1.0 g, 4.51 mmol) and hydroxylamine hydrochloride (1.5 eq, 0.47 g, 6.77 mmol) in ethanol (10 ml) was added N-ethyl-N-isopropylpropan-2-amine (1.6 eq, 1.26 ml, 7.22 mmol) and refluxed at 80° C. for 12 hours under N2. Allow to cool to rt. Dilute with EtOAc (25 ml), wash with water (25 ml), brine (25 ml), dry, concentrate in vacuo afforded (Z)-3-chloro-N′-hydroxy-4-(trifluoromethoxy)benzimidamide (0.71 g, 62.1%, white solid). Used crude in the next step. HRMS(B) m/z 254.0070

Workup

  1. temperatureto cool to rt
  2. washwash with water (25 ml), brine (25 ml)
  3. customdry
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f649e413bff241dc97b169e89c7d8413
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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