1-Decanol → HCID 69687043, compound

HRID 1005558Notes

Reaction equation

HRID 1005558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][OH:23])=[N:12][C:11]=2[CH:24]([CH3:26])[CH3:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:27]([C:31]([O-:33])=[O:32])[C:28]([O-:30])=O.[CH2:34](O)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C(=O)=NC(Cl)=O>>[NH:27]([C:28]([O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:24]([CH3:26])[CH3:25])[N:12]=1)=[O:30])[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:32]

Participants

5

Reactant 4

HCID 81741-DecanolHCID 119708Isocyanatocarbonyl chlorideHCID 9844329{5-[(3,5-Dichlorophenyl)sulfanyl]-4-isopropyl-1-((pyridin-4-YL)methyl)imidazol-2-YL}methanolHCID 21889107HCID 21889107, compound

Product 1

HCID 69687043HCID 69687043, compoundYield 83%

Procedure

The compound 89 (245 mg, 0.6 mmol) was converted to the iminodicarboxylate with N-decanyloxycarbonyl isocyanate prepared from 1-decanol (175 mg, 1.10mmol) and N-chlorocarbonylisocyanate (106 mg, 1 mmol) in the same manner as the example 82 to give the compound 99 (315 mg, 83%). Mp. 105-107° C. Rf 0.39 (EtOAc). 1H-NMR (CDCl3): δH0.88 (3 H, t like, CH3), 1.25-1.30 (14 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 (2H, s, NCH2), 5.31 (2H, s, OCH2), 6.71 (2H, d, J 1.8 Hz, arom 2- and 6-H), 6.77 (2 H, d-like, 4-pyridyl 2- and 6-H), 6.99 (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 : 3424 (NH), 1807 and 1739 (OOCNCOO). Elementary analysis (for C31H40N4O4SCl2) Calcd. : C, 58.58% H, 6.34% N, 8.81% S, 5.04% Cl, 11.15% Found: C, 58.57% H, 6.37% N, 8.77% S, 5.02% Cl, 10.88%

Sources & evidence

ORD record
ord-f140677ad1164ae09417a9a53c80cfbc
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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