N-bromobutanimide → HCID 10029197, compound

HRID 1198927Notes

Reaction equation

HRID 1198927 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].[Br:28]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:12]2[S:13][C:14]([Br:28])=[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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10025528HCID 10025528, compound

Product 1

HCID 10029197HCID 10029197, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A 0.3 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 0.137 g of N-bromosuccinimide were dissolved in 30 ml of anhydrous tetrachloromethane, and the mixture was refluxed for 2 hours. The solvent was distilled off under reduced pressure and the residual solid obtained was purified by silica gel column chromatography (eluent:chloroform:n-hexane=2:1) to afford 0.30 g of 1-ethoxycarbonylmethyl-3-(3,4-dichlorobenzyl)-6-bromo-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-dione having m.p. of 165.5° to 167° C. in a yield of 85%.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residual solid obtained
  4. customwas purified by silica gel column chromatography (eluent:chloroform:n-hexane=2:1)

Sources & evidence

ORD record
ord-c88f7acbf26f4b10bf866a402408dbd8
Source dataset
uspto-grants-1990_02
Patent number
US04898867

Reaction notes

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