Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Chloroacetyl chloride | HCID 6577 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 43119856 | HCID 43119856 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59432880 | HCID 59432880 | 70.6% |
Reaction Steps
To a stirring solution of 2,3-dihydro-1H-indole-5-sulfonic acid thiazol-2-ylamide (2.35 g, 8.36 mmol) in DMF (10 mL), at −75° C., was added triethylamine (1.16 mL, 8.36 mmol) followed by chloroacetyl chloride (1.88 g, 16.7 mmol). The mixture was stirred at −75° C. for 1 h. The reaction showed product formation by LC/MS (10-99% CH3CN). After quenching with MeOH and allowing the mixture to warm to room temperature, the solvents were removed in vacuo. The mixture was purified via column chromatography (2% MeOH in CH2Cl2) to obtain the desired amide (1.95 g, 5.9 mmol, 70% yield). LC/MS (10-99% CH3CN), M/Z: M+1 obs=359.3; tR=2.46 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07786137B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-a2ff8248fba340759206a0d581e96349 |
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| Source note | uspto-grants-2010_08 |
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