Chloroform → HCID 20294030, compound

HRID 2163516Notes

Reaction equation

HRID 2163516 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[CH:7][S:8][CH:9]=1)(=[O:3])[CH3:2].[C:10]([O-])(=[O:12])[CH3:11].[Na+].C(Cl)(Cl)Cl>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:1]([N:4]([C:10](=[O:12])[CH3:11])[C:5]1[N:6]=[CH:7][S:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 517045Sodium AcetateHCID 202940374-Acetamidothiazole

Product 1

HCID 20294030HCID 20294030, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-acetylaminothiazole (2.85g, 20mM) in a mixture of acetic anhydride (30ml) and pyridine (10 ml) was heated at 100° C. for 16 hours. The reaction mixture was cooled and poured onto an ice cold mixture of 20% aqueous sodium acetate (200ml) and chloroform (200 ml.). The layers were separated the organic layer was washed with water, dried (MgSO4) and the solvents removed under vacuum to give an oil. Trituration with hexane followed by recrystallisation from di-isopropyl ether gave the title compound (1.8g, 49%) m.p. 55° C. (Found: C, 45.8; H, 4.4; N, 15.5%. C7H8N2O2S requires: C, 45.6; H, 4.4; N, 15.2%)

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe layers were separated the organic layer
  3. washwas washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvents removed under vacuum
  6. customto give an oil
  7. customTrituration with hexane followed by recrystallisation from di-isopropyl ether

Sources & evidence

ORD record
ord-058e74345921492385504aa93516b2e6
Source dataset
uspto-grants-1979_01
Patent number
US04134984

Reaction notes

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