Benzoyl chloride → HCID 23072338, compound

HRID 1182488Notes

Reaction equation

HRID 1182488 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH2:26][OH:27].Cl>C(N(CC)CC)C>[OH:27][NH:26][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 741934-Phenoxybenzoyl chlorideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 23072338HCID 23072338, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 1, step 4, but substituting 4-phenoxybenzoic acid for 5, followed by Example 18, step 2, 3, but substituting 4-phenoxybenzoyl chloride for benzoyl chloride, and then the resulting carboxylic acid was substituted for 37 in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 104 obtained in 44% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 7.81 (d, J=8.7 Hz, 2H), 7.23 (m, 2H), 7.08 (m, 1H), 6.94 (d, J=8.1 Hz, 2H), 6.87 (d, J=8.1 Hz, 2H), 2.81 (t, J=7.2 Hz, 2H), 1.99 (m, 2H), 1.59 (m, 2H), 1.52 (m, 2H), 1.25 (m, 4H). 13C NMR (75 MHz, 20% CD3OD in CDCl3): δ 24.00, 25.02, 28.56(2), 32.48, 37.96, 116.99, 119.89, 124.41, 129.79, 130.15, 131.15, 155.11, 161.83, 171.14, 199.86.

Sources & evidence

ORD record
ord-74499ff7f103415f8364f8fbbfd806bb
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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