1,4-Bis(bromomethyl)benzene → 5-(4-Bromomethylbenzyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 1591981Notes

Reaction equation

HRID 1591981 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][NH:8][S:7]1(=[O:13])=[O:12].C1CCN2C(=NCCC2)CC1.[Br:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=1>C(Cl)Cl>[Br:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:8]2[S:7](=[O:13])(=[O:12])[N:6]([CH2:5][C:4]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=3[O:2][CH3:1])[C:10](=[O:11])[CH2:9]2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 693351,4-Bis(bromomethyl)benzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66751042HCID 66751042, compound

Product 1

HCID 671395385-(4-Bromomethylbenzyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title B compound in Example 9, 2,4-dimethoxybenzyl-1,1-dioxo-1,2,5-thiadiazolidin-3-one (2.0 g, 6.98 mmol) in CH2Cl2 (100 mL) is treated with DBU (1.06 g, 6.98 mmol). α, α′-Dibromo-p-xylene (9.2 g, 34.9 mmol) is added and the mixture is stirred at RT for 16 h. The mixture is filtered and the filtrate is concentrated to 20 mL. The mixture is chromatographed on silica gel using CH2Cl2 as the eluent. The residual α, α′-dibromo-p-xylene is removed from the product by triturating with Et2O to afford 5-(4-bromomethyl-benzyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a white solid: [M+H]+=469.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated to 20 mL
  3. customThe mixture is chromatographed on silica gel
  4. customThe residual α, α′-dibromo-p-xylene is removed from the product
  5. customby triturating with Et2O

Sources & evidence

ORD record
ord-5d504458e6df4374a2f0112ec7445e21
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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