2-Aminooxazole → 9H-Thioxanthene-9-carboxylic acid oxazol-2-ylamide

HRID 1358415Notes

Reaction equation

HRID 1358415 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[CH:5][N:6]=1.[CH:7]1[C:20]2[CH:19]([C:21](Cl)=[O:22])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:12][C:11]=2[CH:10]=[CH:9][CH:8]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[O:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][C:21]([CH:19]1[C:20]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[S:12][C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:22]

Participants

5

Reactant 2

HCID 5585212-AminooxazoleHCID 125156589H-Thioxanthene-9-carbonyl chloride

Product 1

HCID 539127719H-Thioxanthene-9-carboxylic acid oxazol-2-ylamideYield 18.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of (0.048 g, 0.575 mmol) 2-amino-oxazole [Cockerill & al., Synthesis 591(1976)], and DMAP (0.003 g, 0.03 mmol) in pyridine (2 ml) was added at 0° C. (0.100 g, 0.384 mmol) 9H-thioxanthene-9-carbonyl chloride. Stirring was continued at RT for 16 h, the reaction mixture was evaporated and water (5 ml)/sat. NaHCO3 solution (2 ml) was added. The solid was filtered off, dissolved in dichloromethane, dried (MgSO4), and concentrated in vaccuo. The crude material was purified by column chromatobraphy on silica gel (methylene chloride/methanol 40:1) to give the product (0.022 g, 18%) as a white solid, m.p. 188-191° C. and MS: m/e=309.1 (M+H+).

Workup

  1. customthe reaction mixture was evaporated
  2. additionNaHCO3 solution (2 ml) was added
  3. filtrationThe solid was filtered off
  4. dissolutiondissolved in dichloromethane
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vaccuo
  7. customThe crude material was purified by column chromatobraphy on silica gel (methylene chloride/methanol 40:1)

Sources & evidence

ORD record
ord-1cd1e9fc0c0d421aa106bb82e9b01293
Source dataset
uspto-grants-2003_07
Patent number
US06596743B2

Reaction notes

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