2-Chloroethanol → HCID 21705371, compound

HRID 1004420Notes

Reaction equation

HRID 1004420 reaction equation
Cl[CH2:2][CH2:3][OH:4].[CH:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH2:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>O>[CH:11]([NH:18][CH2:2][CH2:3][OH:4])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:8]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 7036BenzhydrylamineHCID 14798Sodium Hydroxide

Product 1

HCID 21705371HCID 21705371, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

In a 500 mL round bottom flask equipped with a condenser and a thermometer, 2-choroethan-1-ol (23.3 grams, 0.39 mol, Kodak), α-aminodiphenylmethane (82.0 grams, 0.45 mol, Fluka), and water (17 mL) were placed. The mixture was heated on a steam bath (ca. 90° C.) for six hours. After cooling to ambient temperature, NaOH (15 grams, 0.37 mol) was added and the mixture heated on a steam bath for 45 minutes at ca. 90° C. Water (50 mL) was then added to the solution. The resulting two-layered mixture was extracted with two 50 mL portions of toluene. The combined toluene extracts were dried over sodium hydroxide pellets and the toluene then removed by rotary evaporation at reduced pressure. The residue was fractionally distilled using a 7.5 inch Vigreux column. The fraction boiling at 175-177° C./2 mm pressure was collected and then recrystallized from hexane. Yield 39.0 g (59% yield). 1H NMR (δ, 360 MHz, CDCl3) 2.32 (bs, 2H, --OH & --NH), 2.74 (m, 2H, --NCH2CH2O--), 3.64 (m, 2H, --NCH2CH2O--) 4.84 (s, 1H, CHPh2) and 7.30 (m, 10H, aromatic H); 13C NMR (δ, 90 MHz, {1H}, CDCl3); 49.5 (--NCH2CH2O--), 61.5 (--NCH2CH2O--) 67.0 (CHPh2), 127.2, 127.3, 128.3 and 147.5 (CHPh2) mp 69-70° C. uncorrected.

Workup

  1. customIn a 500 mL round bottom flask equipped with a condenser
  2. temperatureAfter cooling to ambient temperature
  3. temperaturethe mixture heated on a steam bath for 45 minutes at ca. 90° C
  4. extractionThe resulting two-layered mixture was extracted with two 50 mL portions of toluene
  5. dry with materialThe combined toluene extracts were dried over sodium hydroxide pellets
  6. customthe toluene then removed by rotary evaporation at reduced pressure
  7. distillationThe residue was fractionally distilled
  8. customThe fraction boiling at 175-177° C./2 mm pressure was collected
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-244c8f5094fd4998b7da828ab232481b
Source dataset
uspto-grants-2000_04
Patent number
US06048979

Reaction notes

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