Ethanol → HCID 20501195, compound

HRID 851789Notes

Reaction equation

HRID 851789 reaction equation
Cl.[NH2:2][C:3]1[S:7][N:6]=[C:5]([CH3:8])[CH:4]=1.Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11].O.C(O)C>N1C=CC=CC=1>[C:10]([NH:2][C:3]1[S:7][N:6]=[C:5]([CH3:8])[CH:4]=1)([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10928Ethyl chloroformateHCID 27239183-Methylisothiazol-5-ylamine hydrochloride

Product 1

HCID 20501195HCID 20501195, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 6.10 g (40.5 mmole) of 5-amino-3-methylisothiazole hydrochloride in 200 ml of dry pyridine is added slowly 13.8 g (127 mmole) of ethyl chloroformate. After 2 days the reaction mixture is treated with 20 ml each of water and ethanol. After 40 min., the solution is concentrated in vacuo to a gum, which is further dried by several evaporations of aqueous ethanol. The crude product is dissolved in 75 ml of boiling ethanol to which is added water until the solution clouds. Upon cooling a crystaline solid containing some diacylated material is collected, redissolved in 100 ml of isopropyl alcohol, and treated with 40 ml of approximately 7 N HCl in isopropyl alcohol. After about 2 hours, the solution is concentrated at reduced pressure to an oily residue which is dried by multiple evaporation of ethanol. A solution of the crude solid in approximately 100 ml of water is adjusted to about pH 7 by addition of 2 N aqueous sodium hydroxide, giving the product as a precipitate. After washing with water and drying, 4.71 g (25.3 mmole) of 5-carbethoxyamino-3-methylisothiazole is obtained. Structure assignment is supported by the nmr spectrum.

Workup

  1. concentrationthe solution is concentrated in vacuo to a gum, which
  2. dry with materialis further dried by several evaporations of aqueous ethanol
  3. dissolutionThe crude product is dissolved in 75 ml of boiling ethanol to which
  4. additionis added water until the solution clouds
  5. temperatureUpon cooling a crystaline solid
  6. additioncontaining some diacylated material
  7. customis collected
  8. dissolutionredissolved in 100 ml of isopropyl alcohol
  9. additiontreated with 40 ml of approximately 7 N HCl in isopropyl alcohol
  10. waitAfter about 2 hours
  11. concentrationthe solution is concentrated at reduced pressure to an oily residue which
  12. dry with materialis dried by multiple evaporation of ethanol
  13. additionA solution of the crude solid in approximately 100 ml of water is adjusted to about pH 7 by addition of 2 N aqueous sodium hydroxide
  14. customgiving the product as a precipitate
  15. washAfter washing with water
  16. customdrying

Sources & evidence

ORD record
ord-2c33ac1e698c47938da291f446a5672b
Source dataset
uspto-grants-1983_05
Patent number
US04386211

Reaction notes

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