2-Aminothiazole → 1,1-Bis(phenylsulphonyl)-2-(thiazol-2-ylamino)ethene

HRID 542883Notes

Reaction equation

HRID 542883 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(O[CH:10]=[C:11]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])C>CC(N(C)C)=O>[C:15]1([S:12]([C:11]([S:21]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:23])=[O:22])=[CH:10][NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:13])=[O:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 124009381,1-Bis(phenylsulphonyl)-2-ethoxyethene

Product 1

HCID 202074261,1-Bis(phenylsulphonyl)-2-(thiazol-2-ylamino)etheneYield 44.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-aminothiazole (0.5 g) and 2-ethoxy-1,1-bis(phenylsulphonyl)ethene (1.76 g) in dimethylacetamide (20 ml) was heated at reflux for 3.5 hours. The solution was cooled and poured onto ice (200 g) and then the resulting buff precipitate was filtered off, washed with water and dried in vacuo over phosphorous pentoxide. Recrystallisation from ethyl acetate gave 1,1-bis(phenylsulphonyl)-2-(thiazol-2-ylamino)ethene (0.9 g), m.p. 189°-191° C.

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperatureThe solution was cooled
  3. additionpoured onto ice (200 g)
  4. filtrationthe resulting buff precipitate was filtered off
  5. washwashed with water
  6. dry with materialdried in vacuo over phosphorous pentoxide
  7. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-fca27d4039b14be8a4308d8fcfcf2248
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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