Chloroacetyl chloride → N-Biphenyl-2-yl-2-chloro-acetamide

HRID 2105889Notes

Reaction equation

HRID 2105889 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl:21][CH2:22][C:23](Cl)=[O:24].C([O-])(O)=O.[Na+]>ClCCl.O>[C:10]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:23](=[O:24])[CH2:22][Cl:21]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 70152-AminobiphenylHCID 8471TriethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 1129350N-Biphenyl-2-yl-2-chloro-acetamideYield 14.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-18 °C

Procedure

Triethylamine (26.7 g) was added to a solution of 2-aminobiphenyl (41.4 g) in dichloromethane (248 mL) at room temperature. The solution obtained was cooled to −18° C. and chloracetylchloride (28.8 g) was slowly added. The suspension obtained was further stirred for 1 hour at 0° C. and for 15 hours at room temperature. Dichloromethane (150 mL), ice-water (500 mL), water (500 mL) and saturated aqueous NaHCO3 (150 mL) were added. After stirring, the phases were separated, the organic phase was washed with half-saturated aqueous NaCl (1000 mL) and the aqueous phases were extracted with dichloromethane (250 mL). The combined organic layers were dried (MgSO4) and concentrated under vacuum to a weight of ca. 100 g. After 40 minutes stirring at room temperature, the precipitate was filtered off, washed with dichloromethane (80 mL) and dried under high vacuum to afford N-biphenyl-2-yl-2-chloro-acetamide (8.6 g, 14.5%) as white crystals. The filtrate was further concentrated under reduced pressure to a weight of ca. 115 g and hexane (100 mL) was added dropwise. After 1 hour of stirring at room temperature, the precipitate was filtered off, washed with 3 portions of hexane/dichloromethane 4:1 (22 mL) and dried under high vacuum affording N-biphenyl-2-yl-2-chloro-acetamide (31.2 g, 53.0%) as a grey powder. The filtrate was concentrated under reduced pressure to a weight of ca. 90 g and stirred for 1 hour at room temperature. The precipitate was filtered off, washed with 2 portions of hexane/dichloromethane 4:1 (17 mL) and dried under high vacuum affording N-biphenyl-2-yl-2-chloro-acetamide (10.8 g, 18.3%) as a grey powder.

Workup

  1. customThe solution obtained
  2. customThe suspension obtained
  3. stirringAfter stirring
  4. customthe phases were separated
  5. washthe organic phase was washed with half-saturated aqueous NaCl (1000 mL)
  6. extractionthe aqueous phases were extracted with dichloromethane (250 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated under vacuum to a weight of ca. 100 g
  9. stirringAfter 40 minutes stirring at room temperature
  10. filtrationthe precipitate was filtered off
  11. washwashed with dichloromethane (80 mL)
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-c73553097bb044babb7ac8aebe83c8d7
Source dataset
uspto-grants-2009_08
Patent number
US07579464B2

Reaction notes

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