Triethylamine → 2-(Diaminomethyleneamino)-4-(2-acetoxyacetylaminomethylthiazol-4-yl)thiazole

HRID 1491891Notes

Reaction equation

HRID 1491891 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)[N:7]=1.[C:17]([O:20][CH2:21][C:22](Cl)=[O:23])(=[O:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[N:7]=[C:3]([CH2:2][NH:1][C:22](=[O:23])[CH2:21][O:20][C:17](=[O:19])[CH3:18])[S:4][CH:5]=2)[N:9]=1)[NH2:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 189538084-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 189538872-(Diaminomethyleneamino)-4-(2-acetoxyacetylaminomethylthiazol-4-yl)thiazoleYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole (1.0 g), acetoxyacetyl chloride (0.45 g) and triethylamine (0.93 g) in methylenechloride (30 ml) was stirred with cooling on an ice-water bath for 8 hours. The solvent was removed under reduced pressure. The residue was suspended in water (100 ml). The mixture was neutralized with a saturated aqueous sodium bicarbonate solution and then was extracted with a mixture of ethyl acetate (200 ml) and tetrahydrofuran (60 ml). The extract was dried with magnesium sulfate and then was evaporated. The residue was chromatographed on a silica gel column eluting with chloroform:methanol =10:1. Recrystallization from a mixture of methanol and diisopropyl ether afforded 2-(diaminomethyleneamino)-4-(2-acetoxyacetylaminomethylthiazol-4-yl)thiazole (0.2 g).

Workup

  1. temperaturewith cooling on an ice-water bath for 8 hours
  2. customThe solvent was removed under reduced pressure
  3. extractionwas extracted with a mixture of ethyl acetate (200 ml) and tetrahydrofuran (60 ml)
  4. dry with materialThe extract was dried with magnesium sulfate
  5. customwas evaporated
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with chloroform
  8. customRecrystallization
  9. additionfrom a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-e219180753e94733afe094b1b32d4fe9
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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