1,4-Dibromobutane → HCID 10499756, compound

HRID 1978303Notes

Reaction equation

HRID 1978303 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][CH2:23]Br>CN(C=O)C>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][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

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 2466478HCID 2466478, compound

Product 1

HCID 10499756HCID 10499756, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 0.70 g, 17 mmol), 65 (3.5 g, 14.5 mmol), and 1,4-dibromobutane (37.6 g, 174 mmol) in DMF (40 mL) were combined and worked up by the method of 43. Excess 1,4-dibromobutane was removed by a Kugelrohr apparatus under high vacuum. Column chromatography (7:1 hexane/EtOAc) produced 5.21 g (95%) of 67 as an oil: NMR δ 0.79 (t, 3 H, J=7), 1.46-1.54 (m, 2 H), 1.64-1.78 (m, 4 H), 2.30 (s, 3 H), 2.60 (s, 6 H), 3.11 (t, 2 H, J=7), 3.21 (t, 2 H, J=7), 3.31 (t, 2 H, J=7), 6.93 (s, 2 H). Anal. (C16H26BrNO2S) C, H, N.

Workup

  1. customExcess 1,4-dibromobutane was removed by a Kugelrohr apparatus under high vacuum

Sources & evidence

ORD record
ord-d81830d0f4024ac38688d58498a91311
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

Loading…