Ammonia → HCID 58911782, compound

HRID 874159Notes

Reaction equation

HRID 874159 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]>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

7

Reactant 3

HCID 222AmmoniaHCID 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 μl mol) 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. additiontreated with ethanolic hydrazine (660 μl, 1.0 M, 660 μl mol)
  3. temperatureheated to reflux
  4. additionAfter 1.5 hr a further portion of ethanolic hydrazine was added (660 μl, 1.0 M, 660 μmol)
  5. temperaturereflux
  6. filtrationThe cooled mixture was filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82b476ee6d914dfab6257db5396793fc
Source dataset
uspto-grants-2015_03
Patent number
US08980837B2

Reaction notes

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