Water → HCID 21833817, compound

HRID 1741091Notes

Reaction equation

HRID 1741091 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[C:4]([CH3:17])[CH:3]=1.C(N(CC)CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28].O>ClCCl>[Cl:25][CH2:26][C:27]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][CH:13]=2)=[C:4]([CH3:17])[CH:3]=1)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 18694306HCID 18694306, compound

Product 1

HCID 21833817HCID 21833817, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4'-Amino-2'-methylbiphenyl-4-carboxylic acid (D115, 2.45 g, 10.8 mmol) and triethylamine (3.8 ml, 27.3 mmol) were stirred in dichloromethane (50 ml) as chloroacetyl chloride (1.05 ml, 13.2 mmol) was added dropwise. This mixture was stirred for 3 h, when water (20 ml) was added. After vigorous stirring for 15 min and basification with potassium carbonate solution, the mixture was separated. The aqueous portion was washed with dichloromethane, and acidified with conc. hydrochloric acid. The precipitated solid was filtered off and dried, giving the title compound (1.33 g, 40%) as a grey powder.

Workup

  1. additionwas added dropwise
  2. stirringAfter vigorous stirring for 15 min
  3. custombasification with potassium carbonate solution, the mixture was separated
  4. washThe aqueous portion was washed with dichloromethane
  5. filtrationThe precipitated solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-2421d6836be8487f8297622e1af8b929
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

Loading…