Propylamine → HCID 2466478, compound

HRID 1978301Notes

Reaction equation

HRID 1978301 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].[CH2:14]([NH2:17])[CH2:15][CH3:16].CCCCCC.CCOC(C)=O>C(Cl)Cl.[OH-].[Na+]>[CH2:14]([NH:17][S:9]([C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=1[CH3:13])(=[O:11])=[O:10])[CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 7852PropylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 2466478HCID 2466478, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Mesitylenesulfonyl chloride (12.0 g, 55 mmol) and propylamine (2.96 g, 50 mmol) in CH2Cl2 (60 mL) and 1 N NaOH (60 mL) were combined and worked up by the method of 31. Column chromatography (3:1 hexane/EtOAc) afforded 8.44 g (85%) of 65 as a crystalline solid: mp 53-54° C.; NMR δ 0.86 (t, 3 H, J=7), 1.44-1.51 (m, 2 H), 2.30 (s, 3 H), 2.64 (s, 6 H), 2.86 (q, 2 H), 4.40 (br t, 1 H), 6.96 (s, 2 H). Anal. (C12H19NO2S) C, H, N.

Sources & evidence

ORD record
ord-20059c4c72a34891b4c12e460a78729d
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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