Boron tribromide → HCID 178517671, compound

HRID 452104Notes

Reaction equation

HRID 452104 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

4

Reactant 2

HCID 25134Boron tribromideHCID 178488766HCID 178488766, compound

Product 1

HCID 178517671HCID 178517671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

ORD record
ord-dcedebba48384bd88056ec34524ff0f9
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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