Benzoyl isothiocyanate → HCID 86706795, compound

HRID 876101Notes

Reaction equation

HRID 876101 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1>ClCCl>[NH2:9][C:10]([NH2:12])=[S:11].[C:1]([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 86706795HCID 86706795, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250 mL 3-neck RBF equipped with a condenser, magnetic stirrer, thermo-probe, nitrogen purge and pressure-equilibrated addition funnel was added benzoyl isothiocyanate (25.0 g, 0.150 mol) followed by dichloromethane (100 mL). The mixture was cooled in an ice-water bath at a temperature below 5° C., at which point tetrahydroquinoline (20.4 g, 0.150 mol) and dichloromethane (100 mL) were added slowly over a period of time of about 30 minutes. The ice-water bath was removed and the reaction mixture was stirred under a nitrogen purge overnight. The reaction mixture was then concentrated in vacuo at a temperature of 40° C. to provide a white solid. The solid was dried to constant weight in vacuo at a temperature of 50° C. and a pressure of <1 mTorr in a 93% yield. The solid was determined to have a melting point of 143.6° C.

Workup

  1. customTo a 250 mL 3-neck RBF equipped with a condenser, magnetic stirrer
  2. customthermo-probe, nitrogen purge
  3. additionwere added slowly over a period of time of about 30 minutes
  4. customThe ice-water bath was removed
  5. custompurge overnight
  6. concentrationThe reaction mixture was then concentrated in vacuo at a temperature of 40° C.
  7. customto provide a white solid
  8. customThe solid was dried to constant weight in vacuo at a temperature of 50° C.

Sources & evidence

ORD record
ord-17ed850bc5a649efae89840ed041d58b
Source dataset
uspto-grants-2015_03
Patent number
US08986847B2

Reaction notes

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