Dimethyl Sulfoxide → Carbamic acid, (3-cyanopropyl)-, 1,1-dimethylethyl ester (9CI)

HRID 598859Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C-:13]#[N:14].[K+].CS(C)=O>O>[C:13]([CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])#[N:14]

Participants

Conditions

Temperature: 90 °C

Procedure

To a 250 mL of round-bottom flask was added tert-butyl 3-bromopropylcarbamate (4.0 g, 17 mmol) (commercially available from 3B Scientific Corporation Product List Order Number 3B3-073730), potassium cyanide (1.5 mL, 20 mmol) and 100 mL of DMSO. The reaction mixture was heated at 90° C. for 16 hours. The mixture was then diluted with 100 mL of water, and extracted with 100 mL of EtOAc twice. The extracts were combined, concentrated, and purified by flash chromatography on silica gel (40% EtOAc/hexane) to give tert-butyl 3-cyanopropylcarbamate (1.7 g, 55% yield). MS m/z: 185 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 4.70 (br s, 1H), 3.25 (q, J=6.65 Hz, 2H), 2.40 (t, J=7.24 Hz, 2H), 1.84-1.91 (m, 2H), 1.45 (s, 9H).

Workup

extractionextracted with 100 mL of EtOAc twice
concentrationconcentrated
custompurified by flash chromatography on silica gel (40% EtOAc/hexane)

Sources & evidence

ORD record: ord-057d4e0683b84294a3749ca44e126365
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897619B2

Reaction notes

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