Carbon tetrabromide → 2-[(5-bromopentyl)-thio]-N-butyl-N-methyl acetamide

HRID 726112Notes

Reaction equation

HRID 726112 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:24]([CH3:35])[C:25](=[O:34])[CH2:26][S:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]O)[CH2:21][CH2:22][CH3:23].[Br:36]C(Br)(Br)Br>C(Cl)Cl>[Br:36][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][S:27][CH2:26][C:25]([N:24]([CH2:20][CH2:21][CH2:22][CH3:23])[CH3:35])=[O:34]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 85637568N-butyl-2-[(5-hydroxypentyl)-thio]-N-methyl acetamide

Product 1

HCID 545075012-[(5-bromopentyl)-thio]-N-butyl-N-methyl acetamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6.88 g of triphenyl phosphine were added to a solution of 5.27 g of the product of Step B in 52 ml of methylene chloride and the mixture was cooled to 0° C. to +5° C. under a nitrogen atmosphere. 8.68 g of tetrabromo methane were added with stirring for one hour at 0° C. The reaction mixture was chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-1) to obtain 6.2 g of the expected product.

Workup

  1. temperaturethe mixture was cooled to 0° C. to +5° C. under a nitrogen atmosphere
  2. customThe reaction mixture was chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-1)

Sources & evidence

ORD record
ord-63cde030b1eb4469ae76831235fdcc2f
Source dataset
uspto-grants-1998_01
Patent number
US05707982

Reaction notes

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