Ethyl orthoformate → 6-((5-bromo-6-chloro-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole

HRID 1848230Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH2:22])[C:5]([NH:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]3[N:15]=[C:16]([S:18][CH3:19])[O:17][C:13]=3[CH:12]=2)=[CH:6][C:7]=1[Cl:8].[CH2:23](OC(OCC)OCC)C>C(O)=O>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[N:9]([CH2:10][C:11]3[CH:21]=[CH:20][C:14]4[N:15]=[C:16]([S:18][CH3:19])[O:17][C:13]=4[CH:12]=3)[CH:23]=[N:22][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-bromo-5-chloro-N1-((2-(methylthio)benzo[d]oxazol-6-yl)methyl)benzene-1,2-diamine (622 mg, 2.40 mmol), triethoxymethane (5 mL) and HCOOH (0.08 mL) was stirred at 90° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 1:1 petroleum ether/ethyl acetate to give 6-((5-bromo-6-chloro-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole as a light brown solid (607 mg, 84.5%). 1H NMR (300 MHz, DMSO-d6) δ 8.56 (s, 1H), 8.07 (s, 1H), 8.02 (s, 1H), 7.72 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.34 (d, J=6.6 Hz, 1H), 5.60 (s, 2H), 2.73 (s, 3H). LCMS (ESI) m/z 408 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with 1:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record: ord-29d36959365b43a19e52bf67978613a2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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