Tetrahydrofuran → (4-Methoxy-7-phenyl-benzothiazol-2-yl)-thiourea

HRID 1063008Notes

Reaction equation

HRID 1063008 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][CH:19]=[C:18]([O:28][CH3:29])[C:16]=2[N:17]=1)=[S:11])(=O)C1C=CC=CC=1.C1COCC1.C[O-].[Na+]>CO>[CH3:29][O:28][C:18]1[C:16]2[N:17]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[S:14][C:15]=2[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 222831071-Benzoyl-3-(4-methoxy-7-phenyl-benzothiazol-2-yl)-thiourea

Product 1

HCID 22283244(4-Methoxy-7-phenyl-benzothiazol-2-yl)-thioureaYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzoyl-3-(4-methoxy-7-phenyl-benzothiazol-2-yl)-thiourea (1.3 g, 3.1 mmol) in methanol (20 ml)/THF (40 ml) was added NaOMe (250 mg, 4.6 mmol) and the mixture stirrd for 72 h at r.t. After evaporation of the solvents water (100 ml) was added with stirring followed by aceticacid (1 ml) which caused a solid to precipitate. This solid was collected and on a glass sinter, washed with water (100 ml), followed by EtOAc (30 ml) then finally cyclohexane (30 ml). After drying the title compound was obtained as a white solid (850 mg, 87% yield), MS: m/e=316.2 (M+H+).

Workup

  1. customAfter evaporation of the solvents water (100 ml)
  2. additionwas added
  3. customto precipitate
  4. customThis solid was collected and on a glass sinter
  5. washwashed with water (100 ml)
  6. dry with materialAfter drying the title compound

Sources & evidence

ORD record
ord-254ceb0c37254c79be0bdcc343afd518
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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