2-Propanone, 1-bromo-3-(4-nitrophenyl)- → HCID 20336549, compound

HRID 1706125Notes

Reaction equation

HRID 1706125 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.Br[CH2:9][C:10](=[O:21])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>>[CH3:1][S:2][CH:3]1[N:6]([CH2:9][C:10](=[O:21])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[C:5](=[O:7])[CH2:4]1

Participants

3

Reactant 2

HCID 122323022-Propanone, 1-bromo-3-(4-nitrophenyl)-HCID 126772484-(Methylsulfanyl)azetidin-2-one

Product 1

HCID 20336549HCID 20336549, compound

Procedure

4-Methylthioazetidin-2-one (470 mg., 4 mmole) and 1-bromo-3-p-nitrophenylpropan-2-one (1.05 g., 4.07 mmole) were converted into the title compound using the process described in Example 1.1. The title compound was obtained as a yellow gum (176 mg., 15% yield). νmax (CHCl3): 1765 (β-lactam C=O), 1735 (ketone C=O), 1605 (aromatic C=C), 1530 and 1355 (aromatic NO2) cm-1. δ(CDCl3): 1.98 (s, 3H, SCH3), 2.98 (dd, J 15, J' 3Hz, 1H, β-lactam CHH), 3.42 (dd, J 15, J' 6Hz, 1H, β-lactam CHH), 3.80 (d, J 18Hz, 1H, NCHH), 3.88 (s, 2H, COCH2Ar), 4.38 (d, J 18Hz, 1H, NCHH), 4.82 (dd, J 6, J' 3Hz, 1H β-lactam CH), 7.43 (d, J 8.5Hz, 2H, Ar-H), 8.22 (d, J 8.5Hz, 2H, Ar-H).

Sources & evidence

ORD record
ord-5c2b2395d5cb4a8d8cd23e0222dbf64d
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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