1,3-Benzodioxole-5-carboxylic acid → Diisopropyl Ether

HRID 982245Notes

Reaction equation

HRID 982245 reaction equation
[OH:1][CH:2]([CH2:22][OH:23])[CH:3]([NH:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:24][CH:25]([CH2:45]O)[CH:26](NC(C1NC2C(C=1)=CC=CC=2)=O)C1C=CC=CC=1.C(O)(=O)C1C=CC2OCOC=2C=1.C(Cl)(=O)C(Cl)=O.NC(C1C=CC=CC=1)C(O)CO>C(N(CC)CC)C>[CH:2]([O:24][CH:25]([CH3:26])[CH3:45])([CH3:22])[CH3:3].[OH:1][CH:2]([CH2:22][OH:23])[CH:3]([NH:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 65578Oxalyl chlorideHCID 12701376HCID 12701376, compoundHCID 14650571HCID 14650571, compoundHCID 14650578HCID 14650578, compound

Product 2

HCID 7914Diisopropyl EtherHCID 14650578HCID 14650578, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-[(1RS, 2RS)-2,3-Dihydroxy-1-phenylpropyl]-3,4-methylenedioxybenzamide 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 piperonylic acid (4.6 g), oxalyl dichloride (2.6 cc), (2RS, 3RS)-3-amino-3-phenyl-1,2-propanediol (4.17 g) and triethylamine (10.5 cc), and after the precipitate is washed with distilled water and then with diisopropyl ether, N-[(1RS, 2RS)-2,3-dihydroxy-1-phenylpropyl]-3,4-methylenedioxybenzamide (6 g), m.p. 172° C., is obtained.

Workup

  1. washafter the precipitate is washed with distilled water

Sources & evidence

ORD record
ord-72410abda2a44992a7a802d1898294a4
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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