Amidinothiourea → 4-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

HRID 2379832Notes

Reaction equation

HRID 2379832 reaction equation
Br.C([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=O)[CH2:14]Br)[N:8]=1)(=O)C.[NH2:17][C:18](=[N:20][C:21]([NH2:23])=[S:22])[NH2:19]>CO>[NH2:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[N:23]=[C:21]([N:20]=[C:18]([NH2:19])[NH2:17])[S:22][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 2724563AmidinothioureaHCID 189538712-(Acetylaminomethyl)-6-bromoacetylpyridine hydrobromide

Product 1

HCID 103997684-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazoleYield 42.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(acetylaminometyl)-6-bromoacetylpyridine hydrobromide (3.34 g) and diaminomethylenethiourea (1.01 g) in methanol (50 ml) was refluxed for 10 hours with stirring. The resulting precipitate was collected, dissolved in water (50 ml) and the solution was made basic with aqueous potassium carbonate. The separated product was collected and washed with water to give 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.90 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. customThe resulting precipitate was collected
  3. dissolutiondissolved in water (50 ml)
  4. customThe separated product was collected
  5. washwashed with water

Sources & evidence

ORD record
ord-c28ea22a0310457883012b15a9d1d9a1
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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