Sulfuryl chloride → HCID 10322078, compound

HRID 1198928Notes

Reaction equation

HRID 1198928 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:12]2[S:13][CH:14]=[C:15]([CH3:16])[C:11]=2[C:10](=[O:17])[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[C:8]1=[O:27])=[O:5])[CH3:2].S(Cl)([Cl:31])(=O)=O>ClC(Cl)(Cl)Cl.CCCCCC>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:12]2[S:13][C:14]([Cl:31])=[C:15]([CH3:16])[C:11]=2[C:10](=[O:17])[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[C:8]1=[O:27])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 10025528HCID 10025528, compound

Product 1

HCID 10322078HCID 10322078, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Procedure

A 0.427 g quantity of 1-ethoxycarbonylmethyl-3-(3,4-dichlorobenzyl)-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (compound IV-5) synthesized in Reference Example 6 and 0.162 g of sulfuryl chloride were dissolved in 30 ml of anhydrous tetrachloromethane, and the mixture was allowed to react at 50° to 70° C. for 6 hours. The residue obtained by concentration of the reaction mixture was subjected to silica gel column chromatography using a 2:1 mixture of chroloform and n-hexane as an eluent to afford 0.30 g of 1-ethoxycarbonylmethyl-3-(3,4-dichlorobenzyl)-6-chloro-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-dione having m.p. of 141° to 145° C. in a yield of 65%.

Workup

  1. customto react at 50° to 70° C. for 6 hours
  2. customThe residue obtained by concentration of the reaction mixture

Sources & evidence

ORD record
ord-b9a5e15234d74655a99aeea587c2b7a8
Source dataset
uspto-grants-1990_02
Patent number
US04898867

Reaction notes

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