Hydrochloric Acid → 6-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 567676

反応式

HRID 567676 の反応式
[C:1]([NH:4][C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([NH2:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:17]=1[C:18](Cl)=O.FC1C=CC=C(F)C=1C1OC(=O)C2C=C([N+]([O-])=O)C=CC=2N=1.Cl>C(N(CC)CC)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]=[C:18]([C:17]3[C:16]([F:15])=[CH:24][CH:23]=[CH:22][C:21]=3[F:25])[O:11][C:10](=[O:12])[C:9]=2[CH:13]=1)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 874382,6-Difluorobenzoyl chlorideHCID 170890Benzoic acid, 5-(acetylamino)-2-amino-HCID 212624642-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one

生成物 1

HCID 99488136-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one収率 94%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 22504574Toluene triethylamine溶媒

実験手順

5-Acetamidoanthranilic acid (0.64g) and 2,6-difluorobenzoyl chloride (1.3 g) were reacted in triethyl amine/toluene (1/1) (20 mL) like described for compound (9), reaction time 1 h. Ethyl acetate (50 mL) and HCl-solution (1 mL 4N in 50 mL water) were added resulting in the formation of a precipitate.The mixture was filtered and the residue dissolved in THF followed by evaporation to dryness, subsequent dissolution in hot dioxane followed by precipitation with hexane resulted in colourless crystals of 6-acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (0.98 g), mp.246 C, MS m/e.: 316 M+.

後処理

  1. customresulting in the formation of a precipitate.The mixture
  2. filtrationwas filtered
  3. dissolutionthe residue dissolved in THF
  4. customfollowed by evaporation to dryness, subsequent dissolution in hot dioxane
  5. customfollowed by precipitation with hexane

出典と根拠

ORDレコード
ord-3e485fe52fe24eaab6bc8b1cb4ca842a
出典データセット
uspto-grants-2001_01
特許番号
US06180625B2

関連ノート

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