Ethanol → N5-Thiazol-2-yl-benzothiazole-2,5-diamine

HRID 723955Notes

Reaction equation

HRID 723955 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH2:14])=[S:13])=[CH:7][C:5]=2[N:6]=1.[CH2:15](O)[CH3:16]>>[S:13]1[CH:16]=[CH:15][N:14]=[C:12]1[NH:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([NH2:1])=[N:6][C:5]=2[CH:7]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 10263051N-(2-Amino-1,3-benzothiazol-5-yl)thiourea

Product 1

HCID 10243747N5-Thiazol-2-yl-benzothiazole-2,5-diamine

Procedure

To a solution of ethanol (12 mL) was added the urea compound (Example 18, 50 mg, 0.22 mmol) along with chloroacetyaldehyde (0.12 mL, 0.94 mmol). The resulting mixture was heated at reflux for 24 hours. The mixture was then cooled to room temperature and the solvent was evaporated. Water (25 mL) was added to the residue and the pH was adjusted to 9 using sodium carbonate solution. The mixture was extracted using ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated (18.8 mg, 33%).%). 1H-NMR (CDCl3) δ: 7.66 (d, 1H, J=2.2 Hz), 7.47 (d, 1H, J=8.54), 7.21–7.18 (m, 2H), 6.73 (d, 1H, J=3.9 Hz); MS (ESI) 248.8 (M+1, 100%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. customthe solvent was evaporated
  4. additionWater (25 mL) was added to the residue
  5. extractionThe mixture was extracted
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated (18.8 mg, 33%).%)

Sources & evidence

ORD record
ord-61f0ffd694e54ae5b8fcbf995fa31cb0
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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