1-Isocyanatoadamantane → HCID 52951864, compound

HRID 508610Notes

Reaction equation

[C:1]12([N:11]=[C:12]=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:14]1([C:20]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:23]=[C:22](NC(NC3C=CC=C(C(F)(F)F)C=3)=O)[CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:1]12([NH:11][C:12](=[O:13])[NH:11][CH2:1][CH2:2][CH2:3][C:22]3[CH:21]=[C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:24]([C:25]4[CH:26]=[CH:27][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:29][CH:30]=4)[N:23]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Reactant 2

HCID 20599951-Isocyanatoadamantane

HCID 52951272HCID 52951272, compound

Product 1

HCID 52951864HCID 52951864, compoundYield 84%

Procedure

The titled compound was prepared in 84% yield from 1-adamantyl isocyanate using the procedure detailed for compound 7. mp 139.4-143.5° C. 1H NMR (300 MHz, CDCl3): δ 7.75 (d, J=9 Hz, 2H), 7.37-7.28 (m, 5H), 7.21-7.15 (m, 2H), 6.36 (s, 1H), 5.70-5.64 (m, 2H), 4.68-4.60 (m, 1H), 4.29 (s, 1H), 3.23 (q, J=7 Hz, 2H), 2.78 (t, J=7, 2H), 2.08-1.87 (m, 9H), 1.67-1.59 (m, 6H), 1.29-1.22 (m, 2H). MS (ESI) m/z: 534.25 (M+H+).

Sources & evidence

ORD record: ord-81d98c46429d49e9873631a19249cde6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096532B2

Reaction notes

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