Boron tribromide → HCID 178517671, compound

HRID 706311Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

1-(1H-Benzo[d]imidazol-5-yl)-5-(4-methoxyphenyl)imidazolidin-2-one (308 mg; 1 mmol; 1 eq.) was dissolved in dry CH2Cl2 (20 ml) under Argon atmosphere and cooled to 0° C. BBr3 (0.285 ml; 3 mmol; 3 eq.) was added dropwise. After complete addition, the mixture was stirred for 1 h at 0° C. and then allowed to warm to room temperature. The reaction was quenched with water and the organic layer was separated. The aqueous layer was neutralized by addition of 1N NaOH. The resulting precipitate was filtered off, dried and used without further purification. Yield: 0.174 g (59.2%); MS m/z: 295.1 [M+H]+; 1H-NMR (400 MHz, DMSO d6): 3.04-3.06 (m, 1H); 3.72-3.77 (m, 1H); 5.30-5.33 (m, 1H); 6.62-6.64 (m, 2H); 6.84 (s, 1H); 7.09-7.11 (m, 2H); 7.17-7.19 (m, 1H); 7.34-7.36 (d, 1H, 3J=8.7 Hz); 7.46 (s, 1H); 8.03 (s, 1H); HPLC (P31/98): rt 6.66 min (100%)

Workup

additionAfter complete addition
temperatureto warm to room temperature
customThe reaction was quenched with water
customthe organic layer was separated
additionThe aqueous layer was neutralized by addition of 1N NaOH
filtrationThe resulting precipitate was filtered off
customdried
customused without further purification
customrt 6.66 min (100%)

Sources & evidence

ORD record: ord-d9c5876ab8994b5ebb50da31429e3818
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173885B2

Reaction notes

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