氯甲酸乙酯 → 6-Nitro-5-methyl-2-ethoxy-3,1-benzoxazin-4-one

HRID 22182

反应方程式

HRID 22182 反应方程式
[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]

参与物

4

反应物 2

HCID 10928氯甲酸乙酯HCID 152831726-氨基-2-甲基-3-硝基苯甲酸

产物 1

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

试剂、催化剂与溶剂 1

HCID 1049吡啶溶剂

实验过程

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+).

后处理

  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

来源与证据

ORD记录
ord-7a5418f062a74240945f6ad1b316d8b0
来源数据集
uspto-grants-1995_06
专利号
US05428021

关联笔记

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