Hydrochloric Acid → HCID 14221235, compound

HRID 868174Notes

Reaction equation

HRID 868174 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]#[N:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1.[S:14]1C=CC=C1CC(O)=O.Cl>O>[O:1]=[C:2]1[N:6]([CH2:7][C:8](=[S:14])[NH2:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 159702-Thiopheneacetic acidHCID 933342-Oxo-3(2H)-benzothiazolacetonitrile

Product 1

HCID 14221235HCID 14221235, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred slurry containing 38 grams (0.2 moles) of 2-oxo-3-benzothiazoline acetonitrile, 15.2 grams (0.2 moles) of thiolacetic acid (dried over MgSO4) and 300 ml. of anhydrous ethyl ether, dried hydrogen chloride gas is bubbled through the suspension at -5° to 0° C. for 3 hours. External cooling was removed and the reaction mixture is stirred at 25°-30° C. for 18 hours. The solid is collected by filtration, washed with 500 ml. of anhydrous ethyl ether and air-dried at 25°-30° C. for one hour. The solid (41 grams) was slurried with 700 ml. of water for one hour. After the addition of 300 ml. of water and 25 grams (0.25 moles) of concentrated hydrochloric acid stirring is continued at 25°-30° C. for another hour. The solid is collected by filtration, washed with water until neutral and air-dried at 25°-30° C. The product, 2-oxo-3-benzothiazoline ethanethioamide, mp. 205°-207° C. with decomposition, is obtained in 85% yield. After recrystallization from heptane/tetrahydrofuran (1:1), it melted at 216°-217° C.

Workup

  1. customof anhydrous ethyl ether, dried hydrogen chloride gas is bubbled through the suspension at -5° to 0° C. for 3 hours
  2. temperatureExternal cooling
  3. customwas removed
  4. filtrationThe solid is collected by filtration
  5. washwashed with 500 ml
  6. dry with materialof anhydrous ethyl ether and air-dried at 25°-30° C. for one hour
  7. waitof water for one hour
  8. additionAfter the addition of 300 ml
  9. filtrationThe solid is collected by filtration
  10. washwashed with water until neutral and
  11. customair-dried at 25°-30° C

Sources & evidence

ORD record
ord-6c3ac23603b449588468e68949731d3c
Source dataset
uspto-grants-1988_10
Patent number
USRE032769

Reaction notes

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