Thionyl Chloride → 4-[5-(2,4-Dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoyl chloride

HRID 1591978Notes

Reaction equation

HRID 1591978 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[S:10](=[O:12])(=[O:11])[N:9]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH2:8][C:7]1=[O:23].O=S(Cl)[Cl:32]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[S:10](=[O:12])(=[O:11])[N:9]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([Cl:32])=[O:19])=[CH:16][CH:15]=2)[CH2:8][C:7]1=[O:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67138314HCID 67138314, compound

Product 1

HCID 865910374-[5-(2,4-Dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.66 g (3.47 mmols) of the title A compound, 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid and 2.5 mL (34 mmol) of SOCl2 in 40 mL toluene are heated at 110° C. until only a small amount of dark solid remained undissolved. The solution is filtered and the solvent is removed on a rotary evaporator and the residual dark purple solid is dried in a vacuum oven overnight to give 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoyl chloride which is used as such without further purification.

Workup

  1. filtrationThe solution is filtered
  2. customthe solvent is removed on a rotary evaporator
  3. customthe residual dark purple solid is dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-628e0ab6b1804262b51610acb91ab43b
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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