Sulfamic Acid → [(2-Hydroxyethyl)phenylamino]-(4-trifluoromethylphenyl)acetonitrile

HRID 406369

Reaction equation

HRID 406369 reaction equation
C[Si]([C:5]#[N:6])(C)C.[F:7][C:8]([F:18])([F:17])[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[C:19]1([NH:25][CH2:26][CH2:27][OH:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S(=O)(=O)(O)N>>[OH:28][CH2:27][CH2:26][N:25]([CH:13]([C:12]1[CH:15]=[CH:16][C:9]([C:8]([F:18])([F:17])[F:7])=[CH:10][CH:11]=1)[C:5]#[N:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 5987Sulfamic AcidHCID 31235N-(2-Hydroxyethyl)anilineHCID 679964-(Trifluoromethyl)benzaldehydeHCID 82115Trimethylsilyl cyanide

Product 1

HCID 66618859[(2-Hydroxyethyl)phenylamino]-(4-trifluoromethylphenyl)acetonitrile

Procedure

Trimethylsilyl cyanide (723 μL) was added to a mixture of 4-(trifluoromethyl)benzaldehyde (CAS #455-19-6, 1 g), N-phenylethanolamine (870 mg) and sulfamic acid (28 mg), and the mixture was stirred at room temperature for 20 hours. The reaction solution was partitioned with water and chloroform. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→1:1) to obtain 775 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customThe reaction solution was partitioned with water and chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-682aa993ee80448d9702b81dc8df3ece
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Linked notes

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