Sulfamide → HCID 54496690, compound

HRID 2379869Notes

Reaction equation

HRID 2379869 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:18])[S:13][C:14]=2[CH2:15]OC)[N:9]=1)[NH2:3].[S:19]([NH2:23])([NH2:22])(=[O:21])=[O:20]>COCCO>[NH2:18][C:12]1[S:13][C:14]([CH:15]=[N:22][S:19]([NH2:23])(=[O:21])=[O:20])=[C:10]([C:8]2[N:9]=[C:5]([N:4]=[C:2]([NH2:3])[NH2:1])[S:6][CH:7]=2)[N:11]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 178494755HCID 178494755, compound

Product 1

HCID 54496690HCID 54496690, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2-(diaminomethyleneamino)-4-[2-(imino)(methoxy)methylthiazol-4-yl]thiazole (1.0 g) and sulfamide (1.36 g) in a 2-methoxyethanol (10 ml) was heated at 70° C. for 7 hours. The resulting precipitate was removed by filtration. The filtrate was chromatographed on a silica gel column eluting with ethyl acetate:methanol=3:1. Recrystallization from a mixture of N,N-dimethylformamide and water afforded 4-[2-(amino)(aminosulfonylimino)methylthiazol-4-yl]-2-(diaminomethyleneamino)thiazole (0.35 g).

Workup

  1. customThe resulting precipitate was removed by filtration
  2. customThe filtrate was chromatographed on a silica gel column
  3. washeluting with ethyl acetate
  4. customRecrystallization
  5. additionfrom a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-d8aa7151a6064d8fa5f2002e7e410d40
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

Loading…