Isothiocyanatotrimethylsilane → Isotiquimide

HRID 247470Notes

Reaction equation

HRID 247470 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.C[Si]([N:16]=[C:17]=[S:18])(C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([C:17](=[S:18])[NH2:16])[C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 75297IsothiocyanatotrimethylsilaneHCID 1856675,6,7,8-Tetrahydro-4-methylquinoline

Product 1

HCID 3037235IsotiquimideYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.55M n-Butyl lithium in hexane (35.5 ml. 55mM) at 0° C. under argon was heated with a solution of N-benzylidine-tert-butylamine (8.85 g, 50mM) in toluene (40 ml) to form lithium N-t-butyl-N-(1-phenylpentyl) amide. After 2 hours a solution of 4-methyl-5,6,7,8-tetrahydroquinoline (7.35 g, 50mM) in toluene (10 ml) was added and after a further 0.5 hours the mixture was heated with a solution of trimethylsilyl isothio-cyanate (7.7 g, 55mM) in toluene (10 ml). After 0.5 hours the reaction was quenched with water, acidified (pH1) with sulphuric acid and the layers separated. The aqueous phase was mixed with an equal volume of cyclohexane and the pH adjusted to 10 with sodium hydroxide solution. The resultant precipitate was removed by filtration, washed with water and cyclohexane and dried in vacuo to give the title compound (7.3 g, 71%) identical with authentic material. (See Example 11 UK Patent Specification No. 1463666).

Workup

  1. customAfter 0.5 hours the reaction was quenched with water
  2. customthe layers separated
  3. additionThe aqueous phase was mixed with an equal volume of cyclohexane
  4. customThe resultant precipitate was removed by filtration
  5. washwashed with water and cyclohexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5b4a85a24f8a4490b8c0ea0dc3ec0a50
Source dataset
uspto-grants-1987_11
Patent number
US04707552

Reaction notes

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