Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Propargyl bromide | HCID 7842 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Acetamide, N-2-benzothiazolyl- | HCID 350459 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 20271328 | HCID 20271328 | 62% |
Reaction Steps
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:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04535088 |
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| Source dataset | uspto-grants-1985_08 |
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| ORD ID | ord-5c5bc91eb8324e07ae3841ffc7c711d8 |
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| Source note | uspto-grants-1985_08 |
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