4-Chlorobenzoic Acid → Diisopropyl Ether

HRID 982244Notes

Reaction equation

HRID 982244 reaction equation
[OH:1][CH:2]([CH2:20][OH:21])[CH:3]([NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O[CH:23]([CH2:43]O)[CH:24](NC(C1NC2C(C=1)=CC=CC=2)=O)C1C=CC=CC=1.ClC1C=CC(C(O)=O)=CC=1.C(Cl)(=O)C(Cl)=O.NC(C1C=CC=CC=1)C(O)CO>C(N(CC)CC)C>[CH:23]([O:1][CH:2]([CH3:3])[CH3:20])([CH3:43])[CH3:24].[OH:1][CH:2]([CH2:20][OH:21])[CH:3]([NH:10][C:11](=[O:19])[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 63184-Chlorobenzoic AcidHCID 65578Oxalyl chlorideHCID 12701376HCID 12701376, compoundHCID 14650571HCID 14650571, compoundHCID 14650576HCID 14650576, compound

Product 2

HCID 7914Diisopropyl EtherHCID 14650576HCID 14650576, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-[(1RS, 2RS)-2,3-Dihydroxy-1-phenylpropyl]-4-chlorobenzamide may be prepared in the following manner: working as in Example 8 for the preparation of N-[(1RS, 2RS)-2,3-dihydroxy-1-phenylpropyl]-2-indolecarboxamide, but starting with 4-chlorobenzoic acid (2.57 g), oxalyl dichloride (1.55 cc), (2RS, 3RS)-3-amino-3-phenyl-1,2-propanediol (2.5 g) and triethylamine (8.3 cc), and after the precipitate is washed with distilled water and then with diisopropyl ether, N-[(1RS, 2RS)-2,3-dihydroxy-1-phenylpropyl]-4-chloro-benzamide (3.2 g), m.p. 142° C., is obtained.

Workup

  1. washafter the precipitate is washed with distilled water

Sources & evidence

ORD record
ord-5055d3e9ccdc495387e95eef3e4fda51
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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