2-Chloroethyl Isothiocyanate → HCID 178478081, compound

HRID 1027691Notes

Reaction equation

HRID 1027691 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH2:17])[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.Cl[CH2:19][CH2:20][N:21]=[C:22]=[S:23]>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([N:17]=[C:22]1[NH:21][CH2:20][CH2:19][S:23]1)[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 1386612-Chloroethyl IsothiocyanateHCID 57814299HCID 57814299, compound

Product 1

HCID 178478081HCID 178478081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)ethanamine (0.30 g, 1.13 mmol) in dichloromethane (6 mL) was added chloroethylisothiocyanate (0.097 mL, 0.988 mmol). The solution was stirred at room temperature for 1.5 hour, and quenched with water. The aqueous layer was extracted with dichloromethane (3×). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. The filtrate was added silica gel, and the solvents were removed under vacuum. Purification by chromatography on silica gel (2 to 10% methanol in dichloromethane) gave a crude material, which was recrystallized in methanol/water to give 1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)-N-(thiazolidin-2-ylidene)ethanamine Compound 18 as a solid (15.9 mg, 0.045 mmol, 4% yield).

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with dichloromethane (3×)
  3. dry with materialThe pooled organic layer was dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. additionThe filtrate was added silica gel
  6. customthe solvents were removed under vacuum
  7. customPurification by chromatography on silica gel (2 to 10% methanol in dichloromethane)
  8. customgave a crude material, which
  9. customwas recrystallized in methanol/water

Sources & evidence

ORD record
ord-a160cc4cdea444eabf34dc13af6b862d
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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