2-Amino-6-methylpyridine → HCID 21506066, compound

HRID 918646Notes

Reaction equation

HRID 918646 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([S:11](=[O:14])(=[O:13])[NH2:12])[C:8](Cl)=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)[CH3:2].[NH2:20][C:21]1[N:26]=[C:25]([CH3:27])[CH:24]=[CH:23][CH:22]=1>>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([S:11](=[O:14])(=[O:13])[NH2:12])[C:8]([NH:20][C:21]2[N:26]=[C:25]([CH3:27])[CH:24]=[CH:23][CH:22]=2)=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 157652-Amino-6-methylpyridineHCID 21506101HCID 21506101, compound

Product 1

HCID 21506066HCID 21506066, compound

Procedure

A mixture of ethyl-4-chloro-3-nitro-5-sulphamyl-benzoate (3.08 g) and 6-amino-2-methyl-pyridine (3.24 g) was melted on an oil bath at 140°C and kept at this temperature for 2 hours, while stirring. The still warm reaction mixture was triturated with ethanol (35 ml) and after cooling, the ethyl-4-(2-methyl-6-pyridylamino)-3-nitro-5-sulphamyl-benzoate was collected by suction and washed with ethanol. After recrystallization from acetonitrile, the compound had a melting point of 203°-204°C.

Workup

  1. customwas melted on an oil bath at 140°C
  2. customThe still warm reaction mixture
  3. customwas triturated with ethanol (35 ml)
  4. temperatureafter cooling
  5. customthe ethyl-4-(2-methyl-6-pyridylamino)-3-nitro-5-sulphamyl-benzoate was collected by suction
  6. washwashed with ethanol
  7. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-a20579cf713140b181beda7df47d795f
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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