Carbon tetrabromide → HCID 19025821, compound

HRID 1033244Notes

Reaction equation

HRID 1033244 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]O)[C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:40][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][N:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][S:18][C:9]1[NH:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=1)[C:25](=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19025802HCID 19025802, compound

Product 1

HCID 19025821HCID 19025821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Part C. A solution of the alcohol prepared in Part B above (4.71 g, 8.93 mmol) and carbon tetrabromide (4.15 g, 12.5 mmol) in methylene chloride (30 mL) was cooled to 0° C., and treated with a solution of triphenylphosphine (3.28 g, 12.5 mmol) in methylene chloride (30 mL) dropwise. After stirring overnight, the solution was evaporated, and the residue was separated by flash chromatography (1:1 ethyl acetatehexane) to afford the product, N-(5-bromopentyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-benzamide, as a low-melting solid (3.71 g, 6.28 mmol, 70%). 1H NMR (CDCl3): 11.08 (1H, br s); 7.61-7.20 (15H, m); 3.66-3.00 (8H, m); 1.98-1.40 (12H, m).

Workup

  1. customthe solution was evaporated
  2. customthe residue was separated by flash chromatography (1:1 ethyl acetatehexane)

Sources & evidence

ORD record
ord-a25fbe5c4b814b46bcf6ab1d0a80c363
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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