Phosgene → 5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 905892Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(Cl)=[O:13]>O1CCOCC1>[Cl:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:12](=[O:13])[NH:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a 250 mL round-bottom flask under N2 was dissolved 2-amino-6-chlorobenzoic acid (11.69 g, 68 mmol) in 100 mL of 1,4-dioxane. The solution was cooled to 0° C. and to this solution was added phosgene (36 ml, 68 mmol) via a dropping funnel The reaction mixture was stirred for 24 hours allowing to warm to 23° C. (rt). The resulting white solid was filtered off and washed with 1,4-dioxane and Et2O. Yield=12.5 g, 93%

Workup

temperatureto warm to 23° C. (rt)
filtrationThe resulting white solid was filtered off
washwashed with 1,4-dioxane and Et2O

Sources & evidence

ORD record: ord-ec25d042770c42778ae889a25601f639
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012968B2

Reaction notes

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