Chlorosuccinimide → 5-Chloro-3-cyano-2-(1,1-dipropoxymethylenamino)thiophene

HRID 1167140Notes

Reaction equation

HRID 1167140 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[N:8]=[C:9]([O:14][CH2:15][CH2:16][CH3:17])[O:10][CH2:11][CH2:12][CH3:13])#[N:2].[Cl:18]N1C(=O)CCC1=O>N1C=CC=CC=1>[Cl:18][C:6]1[S:5][C:4]([N:8]=[C:9]([O:14][CH2:15][CH2:16][CH3:17])[O:10][CH2:11][CH2:12][CH3:13])=[C:3]([C:1]#[N:2])[CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 229958273-Cyano-2-(1,1-dipropoxymethylenamino) thiophene

Product 1

HCID 229958265-Chloro-3-cyano-2-(1,1-dipropoxymethylenamino)thiophene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

In a sulfonation flask, 3.02 g (0.012 mol) 3-cyano-2-(1,1-dipropoxymethylenamino)thiophene, are added, with stirring to 15 ml of absolute pyridine. The internal temperature is then raised to 60° C. and 1.9 g (0.0144 mol) N-chlorosuccinimide are added in three portions. After stirring for 3 hours at 60° C., the pyridine is removed in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed twice with water and after drying, the solvent is removed in a water jet vacuum. The crude product is purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane 1:6). Yield: 3.5 g of 5-chloro-3-cyano-2-(1,1-dipropoxymethyleneamino)thiophene in the form of brownish crystals, m.p. 55-57° C.

Workup

  1. customthe pyridine is removed in a water jet vacuum
  2. washThe organic phase is washed twice with water
  3. customafter drying
  4. customthe solvent is removed in a water jet vacuum
  5. customThe crude product is purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane 1:6)

Sources & evidence

ORD record
ord-ea4c030ac2be460494acd20a634b08e0
Source dataset
uspto-grants-2003_09
Patent number
US06617330B2

Reaction notes

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