phenyl N-(1,3-thiazol-2-yl)carbamate → N-(2-Thiazolyl)-6-chloro-2-oxo-2,3-dihydro-benzo[b]thiophen-3-carboxamide

HRID 434357Notes

Reaction equation

HRID 434357 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][C:8](=[O:10])[S:7][C:6]=2[CH:11]=1.[S:12]1[CH:16]=[CH:15][N:14]=[C:13]1[NH:17][C:18](=O)[O:19]C1C=CC=CC=1>CN(C)P(=O)(N(C)C)N(C)C>[S:12]1[CH:16]=[CH:15][N:14]=[C:13]1[NH:17][C:18]([CH:9]1[C:8](=[O:10])[S:7][C:6]2[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]1=2)=[O:19]

Participants

4

Reactant 2

HCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateHCID 192614186-Chloro-2,3-dihydro-2-oxo-benzo[b]thiophen

Product 1

HCID 20493667N-(2-Thiazolyl)-6-chloro-2-oxo-2,3-dihydro-benzo[b]thiophen-3-carboxamide

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

De-oiled sodium hydride, obtained by de-oiling 0.82 g of a 50% suspension in mineral oil, was added at 10° to a solution of 3 g of 6-chloro-2,3-dihydro-2-oxo-benzo[b]thiophen and 3.85 g of phenyl N-(2-thiazolyl)-carbamate in 30 ml of hexamethylphosphoric acid triamide. After a few minutes, the cooling bath is removed and the mixture is stirred for a further 2 hours at room temperature. The reaction mixture is poured into a mixture of 1 liter of ice-water and 20 ml of concentrated hydrochloric acid, the precipitate is filtered off with suction and washed successively with ice-water, diethyl ether and hexane and taken up in 50 ml of acetone, the acetone solution is heated under reflux, allowed to cool, diluted with 100 ml of diethyl ether and cooled for some time in an ice bath and the precipitate is again filtered off with suction. N-(2-Thiazolyl)-6-chloro-2-oxo-2,3-dihydro-benzo[b]thiophen-3-carboxamide with a melting point of 276°-289° is obtained.

Workup

  1. waitAfter a few minutes
  2. customthe cooling bath is removed
  3. additionThe reaction mixture is poured into a mixture of 1 liter of ice-water and 20 ml of concentrated hydrochloric acid
  4. filtrationthe precipitate is filtered off with suction
  5. washwashed successively with ice-water, diethyl ether and hexane
  6. temperaturethe acetone solution is heated
  7. temperatureunder reflux
  8. temperatureto cool
  9. additiondiluted with 100 ml of diethyl ether
  10. temperaturecooled for some time in an ice bath
  11. filtrationthe precipitate is again filtered off with suction

Sources & evidence

ORD record
ord-e77d4e82ced04f3ba22beae05ee3d04a
Source dataset
uspto-grants-1983_08
Patent number
US04396621

Reaction notes

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