Acetyl chloride → HCID 22647830, compound

HRID 1018747Notes

Reaction equation

HRID 1018747 reaction equation
C(N(CC)CC)C.[CH2:8]([NH:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([O:24][CH3:25])=[C:16]([O:26][CH3:27])[CH:15]=1)[CH2:9][CH2:10][CH3:11].[C:28](Cl)([CH3:30])=[O:29]>C(Cl)Cl>[C:28]([N:12]([CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([O:24][CH3:25])=[C:16]([O:26][CH3:27])[CH:15]=1)[CH2:8][CH2:9][CH2:10][CH3:11])(=[O:29])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22647827HCID 22647827, compound

Product 1

HCID 22647830HCID 22647830, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (350 μL, 2.5 mmol) was added to a solution of aminonaphthalene 19 (250 mg, 0.9 mmol) and AcCl (90 μL, 1.27 mmol) in CH2Cl2 (5 mL) at 0° C. The cooling bath was removed after 10 min, the reaction mixture was stirred for 1 h at room temperature, diluted fivefold with CH2Cl2, washed with an aqueous solution of NaHCO3 followed by 3% HCl, brine and dried (MgSO4). The crude product (315 mg, 100%) obtained after evaporation of the solvent was used in the following step without further purification. 1H NMR (CDCl3) 8.19, 8.15 (2d, J=7.6, 8.4 Hz, 1H), 8.97, 7.80 (2d, J=7.9, 8.2 Hz, 1H), 7.35-7.58 (m, 2H), 7.16, 7.04 (2s, 1H), 5.05, 4.95 (2s, 2H), 4.01, 3.99 (2s, 3H), 3.99, 3.96 (2s, 3H), 3.47, 3.13 (2t, J=7.4, 7.8 Hz, 2H), 2.20, 2.09 (2s, 3H), 1.15-1.70 (m, 4H), 0.91, 0.87 (2t, J=7.2, 7.3 Hz, 3H).

Workup

  1. customThe cooling bath was removed after 10 min
  2. additiondiluted fivefold with CH2Cl2
  3. washwashed with an aqueous solution of NaHCO3
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-874be0b054f34b349862cc1111aaa936
Source dataset
uspto-grants-2002_11
Patent number
US06482943B1

Reaction notes

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