1,3-Dibromopropane → HCID 10642375, compound

HRID 1978302Notes

Reaction equation

HRID 1978302 reaction equation
[H-].[Na+].[CH2:3]([NH:6][S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8])[CH2:4][CH3:5].[Br:19][CH2:20][CH2:21][CH2:22]Br.CCCCCC.CCOC(C)=O>CN(C=O)C>[Br:19][CH2:20][CH2:21][CH2:22][N:6]([CH2:3][CH2:4][CH3:5])[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 2466478HCID 2466478, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10642375HCID 10642375, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 0.34 g, 8.4 mmol), 65 (1.7 g, 7.0 mmol), and 1,3-dibromopropane (17.0 g, 84 mmol) in DMF (30 mL) were combined and worked up by the method of 43. Column chromatography (6:1 hexane/EtOAc) produced 1.82 g (80%) of 66 as an oil: NMR δ 0.79 (s, 3 H), 1.48-1.56 (m, 2 H), 2.04-2.10 (m, 2 H), 2.30 (s, 3 H), 2.60 (s, 6 H), 3.09-3.14 (m, 2 H), 3.29-3.36 (m, 4 H). Anal. (C15H24BrNO2S) C, H, N.

Sources & evidence

ORD record
ord-cf73332c7bb047ba8fa911fb47c5e460
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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