Carbon tetrabromide → HCID 11196186, compound

HRID 327447Notes

Reaction equation

HRID 327447 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:23]([CH2:37][CH2:38][CH3:39])[CH:24]([CH2:27][C:28]1[C:36]2[N:35]=[CH:34][NH:33][C:32]=2[CH:31]=[CH:30][CH:29]=1)[CH2:25]O)[CH2:21][CH3:22].C(Br)(Br)(Br)Br>C(Cl)Cl>[CH2:20]([N:23]([CH2:37][CH2:38][CH3:39])[CH:24]1[CH2:27][C:28]2[C:36]3=[C:32]([N:33]=[CH:34][N:35]3[CH2:25]1)[CH:31]=[CH:30][CH:29]=2)[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15744969HCID 15744969, compound

Product 1

HCID 11196186HCID 11196186, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (625 mg, 2.4 mmol) was added to a stirred solution of β-(dipropylamino)-1H-benzimidazole-4-propanol (600 mg, 2.18 mmol) in methylene chloride (12 mL). After solution was complete, carbon tetrabromide (940 mg, 2.8 mmol) was added and the solution was stirred for 30 minutes. Methylene chloride (20 mL) was added and the solution was extracted with 25 mL 1.0 N hydrochloric acid. The methylene chloride was separated, reextracted with 10 mL 1.0 N HCl, and the combined aqueous extracts were basified (20 mL of 4.0 N NaOH) and extracted with ethyl acetate. After removing the ethyl acetate, the product was chromatographed on silica gel using chloroform as the initial eluant to give 380 mg of product. A sample was crystallized from hexane for analysis; mp 95°-98° C. Anal. Calcd. for C16H23N3 : C, 74.66; H, 9.01; N, 16.33. Found: C, 74.28; H, 9.25; N, 16.36.

Workup

  1. extractionthe solution was extracted with 25 mL 1.0 N hydrochloric acid
  2. customThe methylene chloride was separated
  3. extractionextracted with ethyl acetate
  4. customAfter removing the ethyl acetate
  5. customthe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-ac94b6d1659e4c07be83d49cbecded8f
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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