Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N,N-Dimethylcyclohexylamine | HCID 7415 | — |
| Reactant | Octanoyl chloride | HCID 8124 | — |
| Reactant | N-Hydroxysuccinimide | HCID 80170 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 21832694 | HCID 21832694 | 90% |
Reaction Steps
115.1 g (1 mol) of N-hydroxysuccinimide are introduced into 600 ml of toluene in a round-bottom flask, and 127.3 g (1 mol) of dimethylcyclohexylamine are added. At 60° C., 162.5 g (1 mol) of octanoyl chloride in 180 ml of toluene are added dropwise. The reaction mixture is stirred at 60° C. for 5 hours. Subsequently water is added and the organic phase is washed with water, concentrated hydrochloric acid, water and sodium bicarbonate solution in this order. The organic phase is dried over sodium sulfate, filtered and concentrated. The crystallized residue is dried at 40° C./100 mbar. 219 g (90%) of octanoyloxysuccinimide are obtained with a purity of 99.5%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05972508 |
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| Source dataset | uspto-grants-1999_10 |
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| ORD ID | ord-4797ca81c52c4109b3c696eb05d5d0d3 |
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| Source note | uspto-grants-1999_10 |
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