Ethyl chloroformate → Carbamic acid, (4,5,6,7-tetrahydro-2-benzothiazolyl)-, ethyl ester

HRID 2058859Notes

Reaction equation

HRID 2058859 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13]>N1C=CC=CC=1>[S:3]1[C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=[C:2]1[NH:1][C:12](=[O:13])[O:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazole

Product 1

HCID 17191182Carbamic acid, (4,5,6,7-tetrahydro-2-benzothiazolyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-4,5,6,7-tetrahydrobenzothiazole (12.3 grams; 0.08 mol) dissolved in pyridine (50 ml.) was charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. Ethyl chloroformate (12 ml; 0.11 mol) was added dropwise to the reaction mixture with stirring and cooling. After the addition was completed the reaction mixture was allowed to warm to room temperature and stirring was continued for a period of about 1 hour. After this time the reaction mixture was poured into ice water (50 mol.) to form a precipitate. The precipitate was recovered by filtration, washed with water four times dried and recrystallized from ethanol to yield the desired product ethyl N-(4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate; (16.7 grams); melting point 182°-184° C. The structure of the product was verified by infrared and NMR spectroscopy.

Workup

  1. additionwas 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 was recovered by filtration
  9. washwashed with water four times
  10. customdried
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7a112eec61d44e36b8d727902c43b4dd
Source dataset
uspto-grants-1982_03
Patent number
US04319914

Reaction notes

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