Chlorosuccinimide → 5-Chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole

HRID 1656973Notes

Reaction equation

HRID 1656973 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH:18]=[O:19])=[CH:13][CH:12]=2)[N:8]=1)=[O:2].[Cl:20]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:20][C:6]1[S:5][C:4]([NH:3][CH:1]=[O:2])=[N:8][C:7]=1[CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH:18]=[O:19])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 157291722-Formylamino-4-(4-formylaminophenylthiomethyl)thiazole

Product 1

HCID 157291735-Chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazoleYield 61.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole (2.9 g) in acetic acid (30 ml) was portionwise added N-chlorosuccinimide at 50° C. with stirring. The mixture was heated at 50° C. with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1), washed with water and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 150 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 5-chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole (2.0 g, yield: 61.2%). mp: 130°-150° C. (dec.) IR (Nujol): 3350, 3200, 1710, 1690-1640, 1590 cm-1

Workup

  1. customat 50° C.
  2. stirringwith stirring
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was triturated with water
  5. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1)
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure
  9. customto give solid
  10. washeluted with a mixture of chloroform and methanol (10:1)
  11. additionThe fractions containing the objective compound
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8deda4228fa04835be98e0e21bc3f533
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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