Hydrochloric Acid → N-(3-chlorophenyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophenecarboxamide

HRID 434354Notes

Reaction equation

HRID 434354 reaction equation
[O:1]=[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1.[H-].[Na+].[Cl:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=O)[O:22]C2C=CC=CC=2)[CH:17]=[CH:18][CH:19]=1.Cl>CN(C)P(=O)(N(C)C)N(C)C>[Cl:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]([CH:3]2[C:2](=[O:1])[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]2=3)=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 232110Phenyl hydrogen (3-chlorophenyl)carbonimidateHCID 591560Benzo[b]thiophen-2(3H)-one

Product 1

HCID 12805879N-(3-chlorophenyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 18.2 g of 2,3-dihydro-2-oxo-benzo[b]thiophene in 60 ml of hexamethylphosphoric acid triamide is added dropwise to a suspension of 5.9 g of a 50% strength sodium hydride/mineral oil suspension in 180 ml of hexamethylphosphoric acid triamide, whilst cooling, the reaction temperature being kept below 15°. After stirring for one hour at room temperature, 30.4 g of phenyl N-(3-chlorophenyl)-carbamate are added in portions, with external cooling. The mixture is stirred for a further 16 hours at room temperature and poured onto a mixture of 100 ml of 2 N hydrochloric acid and 1,000 g of ice, whereupon an oil separates out; this oil crystallises on leaving to stand for several hours. The crystals are collected and dissolved in 300 ml of diethyl ether. The solution is washed with water and the organic phase is separated off, dried over sodium sulphate and evaporated to dryness. The residue is recrystallised from ether and gives N-(3-chlorophenyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophenecarboxamide with a melting point of 175°-177°.

Workup

  1. temperaturewhilst cooling
  2. custombeing kept below 15°
  3. stirringThe mixture is stirred for a further 16 hours at room temperature
  4. customthis oil crystallises
  5. customon leaving
  6. waitto stand for several hours
  7. customThe crystals are collected
  8. dissolutiondissolved in 300 ml of diethyl ether
  9. washThe solution is washed with water
  10. customthe organic phase is separated off
  11. dry with materialdried over sodium sulphate
  12. customevaporated to dryness
  13. customThe residue is recrystallised from ether

Sources & evidence

ORD record
ord-88ed4ac0930246eda3e30275138a9f2c
Source dataset
uspto-grants-1983_08
Patent number
US04396621

Reaction notes

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