1-(2-Amino-benzothiazol-5-yl)-3-benzoyl-thiourea → N-(2-Amino-1,3-benzothiazol-5-yl)thiourea

HRID 723953Notes

Reaction equation

HRID 723953 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17]C(=O)C3C=CC=CC=3)=[S:16])=[CH:10][C:8]=2[N:9]=1>CO>[NH2:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[CH:10][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 100421591-(2-Amino-benzothiazol-5-yl)-3-benzoyl-thioureaHCID 10942334Sodium Methoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of anhydrous methanol (213 mL) was added sodium methoxide (1.15 g) and 1-(2-amino-benzothiazol-5-yl)-3-benzoyl-thiourea (Example 17, 3.5 g). The resulting mixture was stirred at room temperature for 3 hours. The mixture was concentrated and the residue was poured into water (300 mL). The mixture was extracted using ethyl acetate (3×200 mL). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated (1.61 g, 67%). 1H-NMR (DMSO d6) δ: 9.64 (s, 1H), 760–7.37 (m, 6H), 6.96 (d, 1H, J=8.3 Hz); MS (ESI) 224.8 (M+1, 100%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was poured into water (300 mL)
  3. extractionThe mixture was extracted
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated (1.61 g, 67%)

Sources & evidence

ORD record
ord-2d147e4a4f77402cb0359c7476e5289c
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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