Chloroform → HCID 20271328, compound

HRID 485043Notes

Reaction equation

HRID 485043 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:16](Br)[C:17]#[CH:18].C(Cl)(Cl)Cl>CN(C)C=O>[C:1]([N:4]([C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[C:16]#[C:17][CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 350459Acetamide, N-2-benzothiazolyl-

Product 1

HCID 20271328HCID 20271328, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Acetylaminobenzothiazole (e) (6.0 g) was dissolved in dimethylformamide (50 ml) and 50% sodium hydride (1.648 g) was added thereto in small portions with stirring under ice-cooling. The mixture was heated at 50° C. for 1 hour, then cooled to room temperature and 2-propynyl bromide (3.0 ml) was added thereto. The mixture was heated at 60° C. for 4 hours and evaporated to remove the solvent. After addition of water, the residue was extracted with benzene. The extract was washed with water, and evaporated to remove the solvent. The residue was applied to column chromatography on silica gel (120 g) to give 2-(N-acetyl-N-propynylamino)benzothiazole (f) (4.43 g, yield 62%) from chloroform eluate:

Workup

  1. temperaturecooling
  2. temperaturecooled to room temperature
  3. temperatureThe mixture was heated at 60° C. for 4 hours
  4. customevaporated
  5. customto remove the solvent
  6. additionAfter addition of water
  7. extractionthe residue was extracted with benzene
  8. washThe extract was washed with water
  9. customevaporated
  10. customto remove the solvent

Sources & evidence

ORD record
ord-5c5bc91eb8324e07ae3841ffc7c711d8
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

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