Diethyl Ether → HCID 18953886, compound

HRID 2379874Notes

Reaction equation

HRID 2379874 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[NH:11][C:12](=[NH:19])[CH:13]=[CH:14][C:15]=2[CH2:16]OC)[N:9]=1)[NH2:3].[N:20]#[C:21][NH2:22].C(OCC)C>CO>[NH2:19][C:12]1[N:11]=[C:10]([C:8]2[N:9]=[C:5]([N:4]=[C:2]([NH2:3])[NH2:1])[S:6][CH:7]=2)[C:15]([CH:16]=[N:22][C:21]#[N:20])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9864CyanamideHCID 178494524HCID 178494524, compound

Product 1

HCID 18953886HCID 18953886, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(diaminomethyleneamino)-4-[6-(imino)(methoxy)methylpyridin-2-yl]thiazole (4.0 g) and cyanamide (1.2 g) in methanol (80 ml) was stirred for 16 hours at ambient temperature. To the mixture was added a diethyl ether (80 ml) and isolated precipitate was collected by filtration. The precipitate was added to a mixture of ethyl acetate and water and adjusted to pH 9.5 with 20% aqueous potassium carbonate. The precipitate was collected by filtration and recrystallized from a mixture of N,N-dimethylformamide and ethyl acetate to give 4-[6-(amino)(cyanoimino)methylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole (3.04 g).

Workup

  1. customisolated precipitate
  2. filtrationwas collected by filtration
  3. additionThe precipitate was added to a mixture of ethyl acetate and water
  4. filtrationThe precipitate was collected by filtration
  5. customrecrystallized from a mixture of N,N-dimethylformamide and ethyl acetate

Sources & evidence

ORD record
ord-c4cd023f7e62462cb32c1563fc0292b4
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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