1,4-Dibromobutane → HCID 90410761, compound

HRID 1403726Notes

Reaction equation

[C:1]1([NH:7][S:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[O:10]=[S:8]1(=[O:9])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:23][CH2:22][CH2:21][CH2:20][N:11]1[C:12]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl N-phenylsulfamoylcarbamate (2.0 g, 7.35 mmol) and 1,4-dibromobutane (1.6 g, 7.35 mmol) in acetone (30 mL) was added Cs2CO3 (7.2 g, 22.05 mmol) and the mixture was stirred at 60° C. for 48 hours. The reaction mixture was filtered and concentrated under reduced pressure to afford tert-butyl 1,1-dioxo-7-phenyl-1λ6,2,7-thiadiazepane-2-carboxylate as a yellow oil (860 mg, 39%). LCMS (ESI): m/z=271.1 [M−56+H]+.

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0e2031cd5a8b494e8fc84b89a205b7cb
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912219B2

Reaction notes

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