HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon Disulfide → 4-Chlorobenzyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon Disulfide | HCID 6348 | — |
| Reactant | 1-Chloro-4-(chloromethyl)benzene | HCID 7723 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline | HCID 13375562 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-Chlorobenzyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate | HCID 13375540 | 70.1% |
Reaction Steps
In the same manner as described in Example 13 by using (1S,3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (216 mg), 2N NaOH (1.5 ml), CS2 (228 mg), 4-chlorobenzyl chloride (480 mg) and 80% ethanol (5 ml), there is prepared the title compound (292 mg, 70%) as white powder, [α]D20 +136.4° (c=1.1, methanol). NMR (CDCl3, δ): 1.63 (d, J=6.5 Hz, 3H, C1 --CH3), 4.57 (s, 2H, CSSCH2 -C6H4 -p-Cl), Mass m/e: 291 (M+ -CH2C6H4 -p-Cl), 258 (M+ -p-Cl-C6H4 -CH2SH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04612317 |
| Source dataset | uspto-grants-1986_09 |
| ORD ID | ord-7be0c4bac6054791851d90f3dcb5e6e9 |
| Source note | uspto-grants-1986_09 |