2-Methoxy-5-nitroaniline → HCID 20313363, compound

HRID 2419503Notes

Reaction equation

HRID 2419503 reaction equation
[CH2:1]([S:3][C:4]([CH3:14])([CH3:13])[C:5]([CH2:7][C:8]([O:10]CC)=O)=[O:6])[CH3:2].[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:18]=1[NH2:19]>>[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:18]=1[NH:19][C:8](=[O:10])[CH2:7][C:5](=[O:6])[C:4]([S:3][CH2:1][CH3:2])([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 74472-Methoxy-5-nitroanilineHCID 53934448HCID 53934448, compound

Product 1

HCID 20313363HCID 20313363, compoundYield 85%

Conditions

Temperature
150 °C

Procedure

A mixture of 21.8 g of ethyl (2-ethylthio-2-methylpropionyl)acetate obtained in Step 1 of Synthesis Example 1 and 16.8 g of 2-methoxy-5-nitroaniline was stirred in an oil bath at 150° C for four hours under a reduced pressure of 50 to 100 mmHg. The reaction mixture was recrystallized from acetonitrile to obtain 29 g (yield 85%) of Coupler (7) having a melting point of 138° to 140° C.

Workup

  1. customThe reaction mixture was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-feb974b97f324cccb53c017e609db5e5
Source dataset
uspto-grants-1978_08
Patent number
US04106942

Reaction notes

Loading…