Acetic Anhydride → 2-(5-Acetylamino-2-methoxyphenyl)-1,3-dioxolane

HRID 356639Notes

Reaction equation

HRID 356639 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.CN(C1C=[C:25]([CH:26]=[O:27])C(OC)=CC=1)S(C)(=O)=O.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)Cl.[Cl-].[Na+].O>[C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1)(=[O:27])[CH3:25]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18938965HCID 18938965, compoundHCID 18938967HCID 18938967, compound

Product 1

HCID 189389762-(5-Acetylamino-2-methoxyphenyl)-1,3-dioxolaneYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-(5-amino-2-methoxyphenyl)-1,3-dioxolane (an intermediate for the compound of Example 3, 17.3 g, 88.8 mmol) and triethylamine (27 ml, 195.4 mmol) in CH2Cl2 (30 ml) was added dropwise acetic anhydride (9.3 ml, 97.7 mmol) and then stirred for 20 hr. To the mixture was added brine and then extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo to give 2-(5-acetylamino-2-methoxyphenyl)-1,3-dioxolane (21.3 g, >100%) as a brown solid.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b902ba26f0b24360adb789932a69a2b0
Source dataset
uspto-grants-1998_11
Patent number
US05837711

Reaction notes

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