2-Chloroethyl isocyanate → HCID 178478080, compound

HRID 1027690Notes

Reaction equation

HRID 1027690 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]=[O: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][O:23]1)[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 57814299HCID 57814299, compound

Product 1

HCID 178478080HCID 178478080, 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 (6.0 mL) was added chloroethylisocyanate (0.11 mL, 1.29 mol). The solution was stirred at room temperature for one hour. The solvent was removed under vacuum. The residue was added water, acetone, and heated at 100° C. for one hour. The mixture was cooled to room temperature, and basified with NaOH (2M) to pH>7. The aqueous layer was extracted with chloroform/isopropanol (3:1, 3×, 200 mL). 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% saturated ammonia methanol in dichloromethane) gave 1-(2,3-dichlorophenyl)-N-(oxazolidin-2-ylidene)-2-(pyridin-4-yl)ethanamine Compound 17 as a white solid (0.21 g, 0.63 mmol, 56% yield).

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe residue was added water, acetone
  3. temperatureheated at 100° C. for one hour
  4. temperatureThe mixture was cooled to room temperature
  5. extractionThe aqueous layer was extracted with chloroform/isopropanol (3:1, 3×, 200 mL)
  6. dry with materialThe pooled organic layer was dried over magnesium sulfate
  7. filtrationThe mixture was filtered
  8. additionThe filtrate was added silica gel
  9. customthe solvents were removed under vacuum
  10. customPurification by chromatography on silica gel (2% saturated ammonia methanol in dichloromethane)

Sources & evidence

ORD record
ord-fc42daffd2644a67a5f1aa46b727c10f
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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