Acetic Anhydride → 6-Iodo-2-methyl-4H-3,1-benzoxazin-4-one

반응식

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=O)[CH3:13]>>[I:11][C:8]1[CH:9]=[CH:10][C:2]2[N:1]=[C:12]([CH3:13])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

참가 물질

반응물 2

HCID 7918Acetic Anhydride

HCID 72911Benzoic acid, 2-amino-5-iodo-

생성물 1

HCID 9153906-Iodo-2-methyl-4H-3,1-benzoxazin-4-one수율 90%

실험 절차

2-Amino-5-iodobenzoic acid (25.4 g, 96.6 mmol) was added in portions to cold acetic anhydride (100 mL). The suspension was first stirred without cooling, then the resulting thick precipitate was heated at reflux for 1 h (red solution). The product crystallized spontaneously upon cooling. After stirring in ice for 30 min, the crystals were filtered off and washed twice with heptane. The crystals were thoroughly dried at 0.1 mbar/50° C. One obtained 25.1 g (90%) of beige crystals. MS: m/z=287 (M).

후처리

temperaturewithout cooling
temperaturethe resulting thick precipitate was heated
temperatureat reflux for 1 h (red solution)
customThe product crystallized spontaneously
temperatureupon cooling
stirringAfter stirring in ice for 30 min
filtrationthe crystals were filtered off
washwashed twice with heptane
customThe crystals were thoroughly dried at 0.1 mbar/50° C

출처 및 근거

ORD 기록: ord-f1525804138841f4a88333612dbe8237
출처 데이터셋: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07728142B2

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