Isopropyl isocyanate → HCID 19025789, compound

HRID 1033242Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:31]([N:34]=[C:35]=[O:36])([CH3:33])[CH3:32]>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[C:35]([NH:34][CH:31]([CH3:33])[CH3:32])=[O:36])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Part D. A solution of the amine prepared in Part C above (2.92 g, 6.89 mmol) in methylene chloride (50 mL) was cooled to 0° C., and a solution of isopropylisocyanate (0.70 mL, 7.1 mmol) in methylene chloride (20 mL) was added dropwise. The mixture was allowed to stir and slowly warm over 18 hours, then was evaporated. The residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, 1-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-(5-hydroxypentyl)-3-(1-methylethyl)-urea, as a low-melting solid (3.00 g, 5.90 mmol, 86%). 1H NMR (CDCl3): 11.34 (1H, br s); 7.60 (2H, br d, J=7 Hz); 7.48 (2H, br d, J =7 Hz); 7.38-7.20 (6H, m); 4.21 (1H, br d, J=6.6 Hz); 4.02 (1H, br s); 3.82 (1H, octet, J=6.6 Hz); 3.65 (2H, br t, J=7 Hz); 3.32 (2H, t, J=6.4 Hz); 3.12 (2H, t, J=7.5 Hz); 3.01 (2H, t, J=6.6 Hz); 1.81-1.36 (12H, m); 1.06 (6H, d, J=6.6 Hz).

Workup

temperatureslowly warm over 18 hours
customwas evaporated
customThe residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane)

Sources & evidence

ORD record: ord-8fd1c55782e447598dd553db74dd8808
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05310748

Reaction notes

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