Chlorosuccinimide → HCID 69986268, compound

HRID 1167138Notes

Reaction equation

HRID 1167138 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:16][CH2:17][CH3:18])[C:7](=[CH:14][NH2:15])[C:8]2[CH:13]=[CH:12][S:11][C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].[Cl:19]N1C(=O)CCC1=O>N1C=CC=CC=1>[CH2:1]([C:5]1[N:6]([CH2:16][CH2:17][CH3:18])[C:7](=[CH:14][NH2:15])[C:8]2[CH:13]=[C:12]([Cl:19])[S:11][C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69986120HCID 69986120, compound

Product 1

HCID 69986268HCID 69986268, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
70 °C

Procedure

In a sulfonation flask, 0.92 g (3.5 mmol) (2-butyl-3-propyl-3H-thieno [2,3-d] pyrimidine-4-ylidene)methylamine are dissolved in 10 ml of absolute pyridine and heated up to 70° C. Then 0.71 g (5.3 mmol) N-chlorosuccinimide are added and the resulting mixture is heated for 1 h at 70° C. After completion of the reaction, pyridine is removed in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed several times with water and after drying of the organic phase with Na2SO4, the solvent is removed in vacuum. The raw material is purified by column chromatography over silica gel (eluant: hexane/THF 2:1). Yield: 0.95 g of (2-butyl-6-chloro-3-propyl-3H-thieno [2,3-d]pyrimidin-4-ylidene) methylamine in the form of a brown oil (1H-NMR-data see table 5).

Workup

  1. temperaturethe resulting mixture is heated for 1 h at 70° C
  2. customis removed in a water jet vacuum
  3. washThe organic phase is washed several times with water
  4. dry with materialafter drying of the organic phase with Na2SO4
  5. customthe solvent is removed in vacuum
  6. customThe raw material is purified by column chromatography over silica gel (eluant: hexane/THF 2:1)

Sources & evidence

ORD record
ord-0c99c4d872124a8cbb6e3baef6cdd8a5
Source dataset
uspto-grants-2003_09
Patent number
US06617330B2

Reaction notes

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