Ethyl Acetate → HCID 58871552, compound

HRID 597798Notes

Reaction equation

HRID 597798 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])(=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(OCC)(=O)C.CCCCCCC>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:9](=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 67184N-bromobutanimideHCID 19023192HCID 19023192, compound

Product 1

HCID 58871552HCID 58871552, compoundYield 120.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

At 80° C., N-bromosuccinimide (1.43 g, 8.06 mmol) and dibenzoylperoxide (62 mg, 0.25 mmol) were added successively to a solution of N-dodecanoyl-4-methylbenzenesulfonamide (3 g, 8.48 mmol) in tetrachloromethane (75 ml). The reaction mixture was heated for 1 h to 80° C. Another portion of dibenzoylperoxide (100 mg, 0.41 mmol) was added. The reaction mixture was heated another 2 h to 80° C. It was cooled to room temperature and left for 16 h. Ethyl acetate (100 ml) and heptane (100 ml) were added. The solid was removed by filtration. The solvent was removed from the filtrate to give 4.19 g of crude 4-bromomethyl-N-(dodecanoyl)benzenesulfonamide, which was used for the next step, without further purification.

Workup

  1. temperatureThe reaction mixture was heated for 1 h to 80° C
  2. temperatureThe reaction mixture was heated another 2 h to 80° C
  3. customThe solid was removed by filtration
  4. customThe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-9cd5eba7b93f40d7b1939722ff445764
Source dataset
uspto-grants-2011_03
Patent number
US07897560B2

Reaction notes

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