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2-Amino-6-methylbenzothiazole → N-(6-methylbenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 250004
Notes
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Reaction equation

HRID 250004 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[C:12](N1C=CN=C1)([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[S:13]>C(#N)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:9][C:12]([N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)=[S:13])[S:8][C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 173352-Amino-6-methylbenzothiazoleHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 57832767N-(6-methylbenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 6-methylbenzo[d]thiazol-2-amine (1.0 g, 6.2 mmol) in acetonitrile (30 mL) was added 1,1′-thiocarbonyldiimidazole (1.44 g, 8.1 mmol). The reaction was stirred at 50° C. for 18 hours. The reaction was cooled to room temperature and the precipitate was filtered and washed with acetonitrile (2×50 mL). The yellow powder was dried in a vacuum oven (40° C.) for 1 hour to yield N-(6-methylbenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide (1.06 g, 3.86 mmol, 62% yield) and then used in the next step without any further purification or characterization.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashed with acetonitrile (2×50 mL)
  4. customThe yellow powder was dried in a vacuum oven (40° C.) for 1 hour

Sources & evidence

ORD record
ord-b9b72e1a0d9849c38e88c58fffc5f962
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863291B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes