4-(Bromomethyl)benzoic acid → HCID 67138314, compound

HRID 1591976Notes

Reaction equation

HRID 1591976 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].Br[CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[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[S:7](=[O:13])(=[O:12])[N:8]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)[CH2:9][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 225994-(Bromomethyl)benzoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66751042HCID 66751042, compound

Product 1

HCID 67138314HCID 67138314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the title B compound in Example 9, 2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (13.87 g, 48.4 mmol) and 4-bromomethylbenzoic acid (10.42 g, 48.4 mmol) in CH2Cl2 (150 mL) is added DBU (14.5 mL, 96.9 mmol) at once and the mixture is stirred at RT overnight. The reaction mixture is washed two times with 1N aqueous HCl, one time with brine, then dried over anhydrous MgSO4 and concentrated to a small volume to crystallize the product. The solid is collected by filtration, washed with ethyl ether and dried under high vacuum to afford 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid: mp=175-177° C.; [M−1]−=419.

Workup

  1. washThe reaction mixture is washed two times with 1N aqueous HCl, one time with brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated to a small volume
  4. customto crystallize the product
  5. filtrationThe solid is collected by filtration
  6. washwashed with ethyl ether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-e0ad3781da754f8aa01432ab2435ca05
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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