Propargyl bromide → HCID 131717315, compound

HRID 1030965Notes

Reaction equation

[F:1][C:2]1[C:12]([N:13]2[C:21](=O)[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=O)=[CH:11][C:5]2[NH:6][CH2:7][C:8](=[O:10])[O:9][C:4]=2[CH:3]=1.[H-].[Na+].C(Br)C#C.[O:30]1C[CH2:33][CH2:32][CH2:31]1>>[F:1][C:2]1[C:12]([N:13]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)=[CH:14]2)=[CH:11][C:5]2[N:6]([O:30][CH2:31][C:32]#[CH:33])[CH2:7][C:8](=[O:10])[O:9][C:4]=2[CH:3]=1

Participants

Reactant 4

HCID 7842Propargyl bromide

HCID 8028Tetrahydrofuran2×

HCID 24758Sodium hydride

HCID 19819245HCID 19819245, compound

Product 1

HCID 131717315HCID 131717315, compoundYield 74%

Procedure

A solution of 3 g (0.0095 mol) of 2-[7-fluoro-3H-1,4-benzoxazin-2(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione in 5 ml of tetrahydrofuran is added dropwise at 0° C. to a suspension of 0.42 g (0.014 mol, 80% in oil) of NaH in 5 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes at room temperature, 1.6 ml (0.014 mol, 80% in toluene) of propargyl bromide are added dropwise and the mixture is refluxed for 2 hours with stirring. Aqueous working-up gives 2.5 (74% of theory) of 2-[7-fluoro-4-propargyloxy-3H-1,4-benzoxazin-2(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-iso-indole- 1-3, dione having a melting point of 189°-190° C.

Workup

temperaturethe mixture is refluxed for 2 hours
stirringwith stirring

Sources & evidence

ORD record: ord-c58288492b214e6394727e0d87e9e1e6
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108483

Reaction notes

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