Ethyl chloroformate → HCID 20548461, compound

HRID 2058856Notes

Reaction equation

HRID 2058856 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]([C:11]#[N:12])[CH2:9][CH:8]([CH2:13][CH2:14][CH3:15])[CH2:7][C:5]=2[N:6]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>N1C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[NH:1][C:2]1[S:3][C:4]2[CH:10]([C:11]#[N:12])[CH2:9][CH:8]([CH2:13][CH2:14][CH3:15])[CH2:7][C:5]=2[N:6]=1)[CH3:21]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 20548475HCID 20548475, compound

Product 1

HCID 20548461HCID 20548461, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-5-propyl-7-cyano-4,5,6,7-tetrahydrobenzothiazole (0.10 mol) dissolved in pyridine (125 ml.) is charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. Ethyl chloroformate (0.12 mol) is then added dropwise to the reaction mixture with stirring and cooling. After the addition is completed the reaction mixture is allowed to warm to room temperature and stirring is continued for a period of about 1 hour. After this time the reaction mixture is poured into ice water to form a precipitate. The precipitate is recovered by filtration, is dried and recrystallized to yield the desired product ethyl-N-(5-propyl-7-cyano-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate.

Workup

  1. additionis charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. additionthermometer and addition funnel
  4. temperaturecooling
  5. additionAfter the addition
  6. stirringstirring
  7. customto form a precipitate
  8. filtrationThe precipitate is recovered by filtration
  9. customis dried
  10. customrecrystallized

Sources & evidence

ORD record
ord-2e10830acf4240358476801e57f66092
Source dataset
uspto-grants-1982_03
Patent number
US04319914

Reaction notes

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