Diisopropylcarbodiimide → HCID 178458024, compound
Reaction equation
[CH:1]([N:4]=[C:5]=[N:6][CH:7]([CH3:9])[CH3:8])([CH3:3])[CH3:2].[Li][AlH][SeH:12]>>[CH:1]([NH:4][C:5]([NH:6][CH:7]([CH3:9])[CH3:8])=[Se:12])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
N,N′-diisopropylcarbodiimide (0.15 mL, 1.0 mmol) was added to the solution of LiAlHSeH (1.0 mmol) prepared as described above in Example One. The reaction mixture was stirred at 0° C. for one hour. The mixture was extracted with diethyl ether and washed with saturated NaCl solution. The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel with dichloromethane:n-hexane (40:1) to give 0.13 grams (62%) N,N′-diisopropylselenourea as a white crystal; mp 142.6–148.2° C.; C7H16N2Se; IR (KBr) 1515, 1570, 3195, 3246 cm−1; 1H NMR (CDCl3) δ 1.19 (12H, d, J=6.4 Hz, CH3), 4.21 (2H, br s), 6.10 (2H, br s); 13C NMR (CDCl3) δ 22.4, 47.9,176.2; MS (EI): m/z=208 [M+]; HRMS: m/z=208.0478 calcd for C7H16N2Se, found 208.0503.
Workup
- customprepared
- extractionThe mixture was extracted with diethyl ether
- washwashed with saturated NaCl solution
- dry with materialThe organic layer was dried over sodium sulfate
- customevaporated to dryness
- customThe residue was purified by flash chromatography on silica gel with dichloromethane:n-hexane (40:1)
Sources & evidence
- ORD record
- ord-5ed905fe8de74dc98538b5d00f41163e
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07033564B2
Reaction notes
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