Sodium Hydroxide → N-(2-Amino-1,3-benzothiazol-6-yl)thiourea

HRID 723945Notes

Reaction equation

HRID 723945 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH:11][C:12]([NH:14]C(=O)C3C=CC=CC=3)=[S:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH:11][C:12]([NH2:14])=[S:13])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21878462N-[(2-Amino-1,3-benzothiazol-6-yl)carbamothioyl]benzamide

Product 1

HCID 21878483N-(2-Amino-1,3-benzothiazol-6-yl)thioureaYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-(2-amino-benzothiazol-6-yl)-3-benzoyl-thiourea (Example 2, 0.2 g, 0.61 mmol) and 2.0 N NaOH (0.67 mL, 1.34 mmol) in 10 mL of THF was heated at reflux for 4 hours. Upon cooling, a yellow solid precipitated which was filtered. Yield: 66.5%, 1H-NMR (DMSO-d6): δ 9.55 (s, 1H); 7.64 (d, 1H, J=1.8 Hz); 7.44 (s, 2H); 7.27 (m, 2H); 7.03 (dd, 1H, J=8.0, 2.0 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureUpon cooling
  4. customa yellow solid precipitated which
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-bc8317bcceff476ca61e19a38b1a2481
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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