Diisopropylethylamine → HCID 22099535, compound

HRID 1735229Notes

Reaction equation

HRID 1735229 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([Cl:27])[CH:18]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([NH:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([Cl:27])[CH:18]=2)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 22099535HCID 22099535, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.37 g of [1,1'-biphenyl]-2-carbonyl chloride in 10 ml of methylene chloride is added dropwise to an ice cold solution of 1.84 g of methyl 4-amino-2-chlorobenzoate and 1.49 g of N,N-diisopropylethylamine in 50 ml of methylene chloride. The reaction mixture is stirred at room temperature for 18 hours and washed with water, saturated aqueous NaHCO3 and the organic layer dried(Na2SO4). The organic layer is passed through a pad of hydrous magnesium silicate and hexane added at the boil to give 1.1 g of the desired product as a crystalline solid, m.p. 132°-134° C. M+H=365

Workup

  1. washwashed with water, saturated aqueous NaHCO3
  2. additionadded at the boil

Sources & evidence

ORD record
ord-ea2b92fade0141eeb938a6b90a7f37ed
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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