Acetyl chloride → HCID 18953854, compound

HRID 1491874Notes

Reaction equation

HRID 1491874 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[N:12]=[C:13]([N:16]=[C:17]([NH2:19])[NH2:18])[S:14][CH:15]=2)[N:10]=1.[C:20](Cl)(=[O:22])[CH3:21].C(N(CC)CC)C>CN(C)C=O>[C:20]([NH:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[N:12]=[C:13]([N:16]=[C:17]([NH2:19])[NH2:18])[S:14][CH:15]=2)[N:10]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18953926HCID 18953926, compound

Product 1

HCID 18953854HCID 18953854, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-[2-(2-aminoethyl)thiazol-4-yl]-2-(diaminomethyleneamino)thiazole dihydrochloride (1.0 g), acetyl chloride (230 mg) and triethylamine (1.0 g) in N,N-dimethylformamide (30 ml) was stirred with cooling on an ice-water bath for 1 hour. The solvent was removed under reduced pressure. The residue was suspended in water (30 ml). The mixture was alkalized to pH 11 with a saturated aqueous potassium carbonate solution and then was extracted with ethyl acetate. The extract was dried with magnesium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with chloroform:methanol=10:1. Recrystallization from a mixture of methanol, ethyl acetate and diisopropyl ether afforded 4-[2-(2-acetylaminoethyl)thiazol-4-yl]-2-(diaminomethyleneamino)thiazole (0.33 g).

Workup

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

Sources & evidence

ORD record
ord-70b875094caa4bd385509156763cfb09
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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