Acetyl chloride → HCID 58726966, compound

HRID 502558Notes

Reaction equation

HRID 502558 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:6]=2[CH:22]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31]>ClCCl>[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:6]=2[CH:22]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58727212HCID 58727212, compound

Product 1

HCID 58726966HCID 58726966, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

N-(2-(5-Aminobenzo[d]isothiazol-3-ylamino)ethyl)picolinamide (95 mg, 0.30 mmol) was dissolved in anhydrous dichloromethane (5 mL) with triethylamine (50 μL, 0.36 mmol). The solution was cooled on an ice-water bath and a solution of acetyl chloride (26 μL, 0.36 mmol) in dichloromethane (0.5 mL) was added dropwise. The reaction mixture was allowed to stir for 2.5 h while warming to room temperature. The solution was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield N-(2-(5-acetamidobenzo[d]isothiazol-3-ylamino)ethyl) picolinamide as a white solid. 1H NMR (300 MHz, CDCl3): 8.48 (d, 1H), 8.30 (s, 1H), 8.20 (d, 1H), 7.80 (t, 1H), 7.52 (s, 1H), 7.42 (m, 1H), 7.31 (d, 1H), 7.18 (s, 1H), 6.82 (d, 1H), 3.70 (m, 2H), 3.50 (m, 2H), 2.20 ppm (s, 3H). MW=355 confirmed by LC-MS, tr=9.35 min (Method Y) MH+=356.

Workup

  1. temperatureThe solution was cooled on an ice-water bath
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd20541fd1364f6c9f7b7e16dc84777a
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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