Acetic Anhydride → HCID 57859220, compound

HRID 2275508Notes

Reaction equation

HRID 2275508 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:6]=2[NH2:16].[C:17](OC(=O)C)(=[O:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:6]=2[NH2:16])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 137133,9-Acridinediamine

Product 1

HCID 57859220HCID 57859220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL rbf equipped with a nitrogen bubbler were charged 3,9-diaminoacridine (50 mg, 0.24 mmol) and anhydrous DCM (2 mL). To the resulting red suspension was added acetic anhydride (25 μL, 0.26 mmol) followed by triethylamine (37 μL, 0.26 mmol). The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. LCMS showed incomplete reaction but only formation of expected product. Starting material was not really soluble in DCM. Pyridine (0.5 mL) was thus added and the mixture stirred overnight. LCMS still showed incomplete reaction. A further portion of acetic anhydride (25 μL, 0.26 nmol) was added and the reaction mixture was stirred at room temperature over three days. LCMS showed reaction completion.

Workup

  1. customTo a 25 mL rbf equipped with a nitrogen bubbler

Sources & evidence

ORD record
ord-0160c80301c14d07bdd006dcc758d348
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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