Triethylamine → 1-Naphthyl Isothiocyanate

HRID 1454774Notes

Reaction equation

HRID 1454774 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:19](Cl)(Cl)=[S:20]>ClCCl>[C:1]1([N:11]=[C:19]=[S:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86401-NaphthylamineHCID 10040Thiophosgene

Product 1

HCID 110801-Naphthyl Isothiocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of 1-naphthylamine (21.48 g), triethylamine (33.39 g), and dichloromethane (250 mL) was added a dicholomethane (50 mL) solution of thiophosgen (18.97 g) at bleow 20° C. over 30 minutes, and the mixture was stirred at room temperature. The reaction mixture was added into ice-water (1000 mL), extracted with diethyl ether (1000 mL). The extract was washed two times with brine (1000 mL), dried over anhydrous magnesium sulfate, evaporated under reduced pressure to obtain crude (1-naphthyl)isothiocyanate.

Workup

  1. extractionextracted with diethyl ether (1000 mL)
  2. washThe extract was washed two times with brine (1000 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-11af1ef5c2fa4cfa8777274a0ddec22a
Source dataset
uspto-grants-2009_01
Patent number
US07482339B2

Reaction notes

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