Ammonium Chloride → HCID 57546216, compound

HRID 913975Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:12]=[C:13]([CH:14]=[O:15])[C:8]=3[N:7]=[CH:6]2)[CH2:3][CH2:2]1.[CH3:20][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[C:11]([C:16]([F:18])([F:19])[F:17])[CH:12]=[C:13]([CH:14]([OH:15])[CH3:20])[C:8]=3[N:7]=[CH:6]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(Cyclopropylmethyl)-6-(trifluoromethyl)-1H-benzo[d]imidazole-4-carbaldehyde (0.323 g, 1.2 mmol) was dissolved in tetrahydrofuran (6 mL), cooled down to 0° C. and to it was added methylmagnesium bromide (1.0 M in dibutyl ether, 2.2 mL, 2.2 mmol) dropwise. After 1.5 h, saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate (3×30 mL). The organic layer was washed with water (20 mL), brine (20 mL) and dried (Na2SO4). The crude product obtained after evaporation of solvent was purified by flash chromatography on silica gel (2% MeOH/CH2Cl2) affording 286 mg (84%) of product as light yellow oil. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 8.11 (s, 1 H), 7.62 (s, 1 H), 7.46 (s, 1 H), 5.38-5.49 (m, 1 H), 4.16 (d, J=6.1 Hz, 1 H), 4.06 (d, J=7.0 Hz, 2 H), 1.70 (d, J=6.7 Hz, 3 H), 1.29-1.40 (m, 1 H), 0.69-0.80 (m, 2 H), 0.45 (q, J=5.2 Hz, 2 H). 308.17 (MNa)+.

Workup

extractionthe mixture was extracted with ethyl acetate (3×30 mL)
washThe organic layer was washed with water (20 mL), brine (20 mL)
dry with materialdried (Na2SO4)
customThe crude product obtained
customafter evaporation of solvent
customwas purified by flash chromatography on silica gel (2% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-8e81e810886245ff8314d33daacd791a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026257B2

Reaction notes

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