Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Stearyl Alcohol | HCID 8221 | — |
| Reactant | Isocyanate | HCID 105034 | — |
| Reactant | {5-[(3,5-Dichlorophenyl)sulfanyl]-4-isopropyl-1-((pyridin-4-YL)methyl)imidazol-2-YL}methanol | HCID 9844329 | — |
| Reactant | HCID 21889107 | HCID 21889107 | — |
| Product | HCID 69686684 | HCID 69686684 | 66% |
Reaction Steps
The compound 89 (245 mg, 0.6 mmol) was converted to the iminodicarboxylate with N-octadecanyloxycarbonyl isocyanate prepared from 1-octadecanol (297 mg, 1.1 mmol) and N-chloroarbonyl isocyanate (106 mg, 1 mmol) in the same manner as the example 82 to give the compound 100 (295 mg, 66%). Mp. 96-98° C. Rf 0.46 (EtOAc). 1H-NMR (CDCl3): δH0.88 (3 H, t like, CH3), 1.25-1.30 (30 H, m, --CH2 --), 1.31 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.62 (2 H, m, --CH2 --), 3.18 (1 H, sep, J 6.9 Hz, (CH3)2CH), 4.14 (2 H, t, J 6.9 Hz, CH2O), 5.23 (2 H, s, NCH2), 5.31 (2 H, s, OCH2), 6.71 (2 H, d, J 1.8 Hz, arom 2- and 6-H), 6.77 (2 H, d-like, 4-pyridyl 2- and 6-H), 6.95 (1 H, bs, NH), 7.06 (1 H, t, J 1.8 Hz, arom 4-H), 8.45 (2 H, d-like, 4-pyridyl 3- and 5-H). IR(CHCl3)cm-1 : 3394 (NH), 1791 and 1764 (NCO), 1715 (NCOO). Elementary analysis (for C39H56N4O4SCl2) Calcd. : C, 62.64% H, 7.55% N, 7.49% S, 4.29% Cl, 9.48% Found: C, 62.86% H, 7.73% N, 7.43% S, 4.00% Cl, 9.07%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06054591 |
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| Source dataset | uspto-grants-2000_04 |
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| ORD ID | ord-2297c2e56d5647ccb2a2dc5205822871 |
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| Source note | uspto-grants-2000_04 |
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