Ethyl chloroformate → 6-Nitro-5-methyl-2-ethoxy-3,1-benzoxazin-4-one

HRID 22182

反応式

HRID 22182 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:14])=[C:8]([C:12]=1[CH3:13])[C:9]([OH:11])=[O:10])([O-:3])=[O:2].Cl[C:16]([O:18][CH2:19][CH3:20])=O>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:14]=[C:16]([O:18][CH2:19][CH3:20])[O:10][C:9](=[O:11])[C:8]=2[C:12]=1[CH3:13])([O-:3])=[O:2]

参加物

4

反応物 2

HCID 10928Ethyl chloroformateHCID 152831726-Amino-2-methyl-3-nitrobenzoic acid

生成物 1

HCID 152831736-Nitro-5-methyl-2-ethoxy-3,1-benzoxazin-4-one収率 79%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 4.0 g (20.4 mmoles) of 5-nitro-6-methyl-2-aminobenzoic acid in 50 mL of dry pyridine was cooled in an ice-water bath under inert atmosphere. Ethyl chloroformate (Aldrich), 10 mL (105 mmoles), was added dropwise over a 15 minute period. A mild exotherm was observed and a solid separated from solution immediately upon addition. The suspension was stirred at room temperature under inert atmosphere overnight. Approximately half the pyridine was removed in vacuo, and the residual mixture poured over ice. The precipitated solid was collected and air-dried. 4.0 g (79% yield) 6-nitro-5-methyl-2-ethoxy-3,1-benzoxazin-4-one was obtained. NMR (DMSO-d6): 1.37(t,3H,J=7.2 Hz), 2.71(s,3H), 4.50(q,2H,J=7.2 Hz), 7.40(d,1H, J=9.0 Hz), 8.19(d,1H,J=9.0 Hz). IR(nujol): 1765 cm-1 (lactone carbonyl). MS(m/z): 250(M+).

後処理

  1. customa solid separated from solution immediately upon addition
  2. customApproximately half the pyridine was removed in vacuo
  3. additionthe residual mixture poured over ice
  4. customThe precipitated solid was collected
  5. customair-dried

出典と根拠

ORDレコード
ord-7a5418f062a74240945f6ad1b316d8b0
出典データセット
uspto-grants-1995_06
特許番号
US05428021

関連ノート

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