HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2373461Generated: October 31, 2026
Diisopropylamine → N,N-Dimethyl-4-trimethylsilanylethynyl-benzamide
https://huagongshe.com/reaction/2373461
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-iodo-N,N-dimethylbenzamide | HCID 879933 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N,N-Dimethyl-4-trimethylsilanylethynyl-benzamide | HCID 69292322 | — |
Reaction Steps
To a mixture under Ar of 4-Iodo-N,N-dimethyl-benzamide (237 mg), trimethylsilylacetylene (169 mg), [PdCl2(PPh3)2] (30 mg) and copper(i) iodide (15 mg) is added a degassed mixture of THF (4.5 ml) and diisopropylamine (4.5 ml). After stirring over night at 57° C. and aqueous work up, the organic layer is dried over Na2SO4 and the solvent is evaporated. Flash chromatography (silica gel, CH2Cl2/MeOH/25% NH4OH 97:3:0.3) yields N,N-Dimethyl-4-trimethylsilanylethynyl-benzamide as a brown oil, 1H-NMR (300 MHz): 0.25 (s, 3H); 2.96 (s, 3H); 3.10 (s, 3H); 7.35 (d, J=8.5, 2H); 7.49 (d, J=8.5, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07459480B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-ef7587fb923647a59990e48118062d96 |
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| Source note | uspto-grants-2008_12 |
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