Trichloroacetonitrile → HCID 57545958, compound

HRID 913976Notes

Reaction equation

HRID 913976 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:12]=[C:13]([CH:14]([OH:16])[CH3:15])[C:8]=3[N:7]=[CH:6]2)[CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[Cl:32][C:33]([Cl:37])([Cl:36])[C:34]#[N:35]>C(OCC)C>[Cl:32][C:33]([Cl:37])([Cl:36])[C:34](=[NH:35])[O:16][CH:14]([C:13]1[C:8]2[N:7]=[CH:6][N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:9]=2[CH:10]=[C:11]([C:17]([F:19])([F:20])[F:18])[CH:12]=1)[CH3:15]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57546216HCID 57546216, compound

Product 1

HCID 57545958HCID 57545958, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

(±)-1-(1-(Cyclopropylmethyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)ethanol (0.283 g, 0.996 mmol) was dissolved in diethyl ether (13 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (341 μL, 2.27 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (300 μL, 2.93 mmol) dropwise over 10 min. The reaction was allowed to warm up to room temperature overnight and concentrated. Flash chromatography on silica gel (50% ethyl acetate/hexanes) gave 195 mg (45.6%) as an light yellow oil. 1H-NMR (500 MHz, CHLOROFORM-D) δ ppm 8.33 (s, 1 H), 8.15 (s, 1 H), 7.69 (s, 1 H), 7.64 (s, 1 H), 6.81 (q, J=6.4 Hz, 1 H), 4.05 (d, J=7.0 Hz, 2 H), 1.82 (d, J=6.4 Hz, 3 H), 1.29-1.39 (m, 1 H), 0.70-0.80 (m, 2 H), 0.40-0.50 (m, 2 H); 19F-NMR (470 MHz, CHLOROFORM-D) δ ppm −61.19.

Workup

  1. temperatureto warm up to room temperature overnight
  2. concentrationconcentrated
  3. customFlash chromatography on silica gel (50% ethyl acetate/hexanes) gave 195 mg (45.6%) as an light yellow oil

Sources & evidence

ORD record
ord-01e82fe86a3a47609ba14605e0274949
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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