Sodium hydride → HCID 10593786, compound

HRID 1978290Notes

Reaction equation

HRID 1978290 reaction equation
[H-].[Na+].[C:3]([CH2:5][CH2:6][CH2:7][NH:8][S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:11])=[O:10])#[N:4].Br[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27].CCCCCC.CCOC(C)=O>CN(C=O)C>[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:8]([CH2:7][CH2:6][CH2:5][C:3]#[N:4])[S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:10])=[O:11])#[N:27]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 794355-BromopentanenitrileHCID 10825665HCID 10825665, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10593786HCID 10593786, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 0.90 g, 23 mmol), 36 (5.02 g, 18.85 mmol), and 5-bromovaleronitrile (2.4 mL, 21 mmol) in DMF were combined and worked up by the method of 43. Column chromatography (1:1 hexane/EtOAc) provided 5.20 g (79%) of 38 as an oil: NMR δ 1.49-1.66 (m, 4 H), 1.82 (m, 2 H), 2.22 (t, 2 H, J=7), 2.25 (t, 2 H, J=7), 2.29 (s, 3 H), 2.57 (s, 6 H), 3.19 (t, 2 H, J=7), 3.29 (t, 2 H, J=7), 6.95 (s, 2 H). Anal. (C18H25N3O2S) C, H, N.

Sources & evidence

ORD record
ord-5aa34c47a4ab432185757ea3ddb79a65
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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