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Benzyl Isothiocyanate → 1,5-Di(benzylthiocarbamoylamino)naphthalene

HRID 758
Notes
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Reaction equation

HRID 758 reaction equation
[C:1]1([NH2:12])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:13]([N:20]=[C:21]=[S:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[CH2:13]([NH:20][C:21]([NH:12][C:1]1[C:10]2[C:5](=[C:6]([NH:11][C:21](=[S:22])[NH:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[S:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 167201,5-Diaminonaphthalene

Product 1

HCID 196932801,5-Di(benzylthiocarbamoylamino)naphthaleneYield 30.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1,5-Naphthalenediamine (0.791 g, 5 mM) was dissolved in 20 ml of ethyl acetate, and 2 equivalents of benzylisothiocyanate (1.492 g, 10 mM) were added. The mixture was stirred at 80° C. for 30 minutes. After cooling, the reaction mixture was filtered, and washed with ethylacetate/n-hexane to obtain 0.70 g (30.7% yield) of a colorless crystal of compound A-29.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washwashed with ethylacetate/n-hexane

Sources & evidence

ORD record
ord-d421bcbbd72f4cb18c2bcf8464545117
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723075

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes