Ammonia → HCID 58911782, compound

HRID 1296184Notes

Reaction equation

HRID 1296184 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[C:6]1([C:12]2[N:13]=[CH:14][S:15][C:16]=2[N:17]2C(=O)C3=CC=CC=C3C2=O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH3:28].NN>ClCCl.CO>[NH2:17][C:16]1[S:15][C:14]([S:1]([NH2:28])(=[O:3])=[O:2])=[N:13][C:12]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:17][C:16]1[S:15][CH:14]=[N:13][C:12]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 9321Hydrazine2×HCID 24648Sulfuryl chlorideHCID 66720753HCID 66720753, compound

Product 2

HCID 470027674-Phenylthiazol-5-aMineYield 16%HCID 58911782HCID 58911782, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The crude mixture of sulfonyl chloride with 4-phenyl-5-phthalimido-thiazole (231 mg) in dichloromethane (10 ml) was treated with ammonia in methanol (900 μl, 2.0 M) dropwise at ambient temperature. After 10 min the mixture was concentrated in vacuo. The residue was suspended in ethanol (10 ml), treated with ethanolic hydrazine (660 μl, 1.0 M, 660 μmol) and heated to reflux. After 1.5 hr a further portion of ethanolic hydrazine was added (660 μl, 1.0 M, 660 μmol) and reflux continued for 15 hr. The cooled mixture was filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded pure 5-amino-2-(aminosulfonyl)-4-phenylthiazole (56 mg, 36% for 3 steps) and 5-amino-4-phenylthiazole (17 mg, 16% for 3 steps).

Workup

  1. concentrationAfter 10 min the mixture was concentrated in vacuo
  2. temperatureheated to reflux
  3. temperaturereflux
  4. filtrationThe cooled mixture was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-217002d3806c42b8ac8e5f334589781f
Source dataset
uspto-grants-2007_07
Patent number
US07244851B2

Reaction notes

Loading…