Acetyl chloride → 2-[(5-Acetylamino-2-pyridinyl)thio]ethyl-3-chlorobenzoate

HRID 731771Notes

Reaction equation

HRID 731771 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([S:12][CH2:13][CH2:14][O:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[N:10][CH:11]=1.C(N(CC)CC)C>ClCCl>[C:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([S:12][CH2:13][CH2:14][O:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[N:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 578381082-[(5-Amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate

Product 1

HCID 578381152-[(5-Acetylamino-2-pyridinyl)thio]ethyl-3-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[(5-nitro-2-pyridinyl)thio]ethyl 3-chlorobenzoate (5) (0.24 g, 0.71 mmol) and 10% Pd/C (0.10 g) in toluene or methanol was agitated under a hydrogen atmosphere (40 PSI) for 1 h. The reaction mixture was filtered through Celite® and concentrated to give 2-[(5-amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate (51), LCMS: purity: 99%; MS (m/e): 309 (MH+), which was used without further purification. Acetyl chloride (4.6 μL, 0.064 mmol) was added to a room temperature solution of 2-[(5-amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate (51) (18.9 mg, 0.061 mmol) and triethylamine (18 μL, 0.13 mmol) in anhydrous dichloromethane (1.0 mL), After 16 h, the reaction mixture was diluted with dichloromethane and washed with 1N HCl and brine and then dried over anhydrous MgSO4. Purification by silica gel chromatography provided 2-[(5-acetylamino-2-pyridinyl)thio]ethyl-3-chlorobenzoate (52), LCMS: purity: 99%; MS (m/e): 351 (MH+).

Workup

  1. customMS (m/e): 309 (MH+), which was used without further purification
  2. washwashed with 1N HCl and brine
  3. dry with materialdried over anhydrous MgSO4
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-55b648b2a91b4266bfc81d485d1567a8
Source dataset
uspto-grants-2009_09
Patent number
US07585883B2

Reaction notes

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