Chloroform → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-bromomethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

HRID 1378862Notes

Reaction equation

HRID 1378862 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].P(Br)(Br)[Br:39].C(Cl)(Cl)Cl.[NH4+].[OH-]>C(OCC)C.C(Cl)Cl.CO>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:39])=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 24614Phosphorus tribromideHCID 19080378N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamide

Product 1

HCID 22912502N-(4-iso-propylbenzenesulfonyl)-alpha-(4-bromomethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.200 g (0.381 mmol) of the product of Example 65 dissolved in 1.5 mL of diethyl ether was added 0.837 mL (0.837 mmole) of 1.0M phosphorus tribromide in methylene chloride solution under nitrogen at 0° C. The reaction mixture was stirred at 0° C. for 2 hours when TLC analysis (80:15:1 CHCl3 --MeOH--NH4OH) indicated that the reaction was nearly complete. The reaction was quenched at 0° C. with water and then partitioned with EtOAc. The aqueous portion was separated and the EtOAc portion was washed with brine (2×10 mL). The EtOAc portion was then dried over MgSO4, filtered, evaporated to a residue, and then used in the next step of the reaction scheme.

Workup

  1. customThe reaction was quenched at 0° C. with water
  2. custompartitioned with EtOAc
  3. customThe aqueous portion was separated
  4. washthe EtOAc portion was washed with brine (2×10 mL)
  5. dry with materialThe EtOAc portion was then dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to a residue
  8. customused in the next step of the reaction scheme

Sources & evidence

ORD record
ord-2164ac6a416d47baae2666c78468c05b
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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