Chlorosuccinimide → HCID 14722569, compound

HRID 2205899Notes

Reaction equation

HRID 2205899 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[NH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:12][C:11]=1[Cl:21]>CC#N>[NH2:9][C:10]1[C:11]([Cl:21])=[CH:12][C:13]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:19][C:20]=1[Cl:8]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 202874814-Amino-3-chloro-N,N-dimethylbenzamide

Product 1

HCID 14722569HCID 14722569, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NCS (38 mg, 0.288 mmol) was added to a solution of 4-amino-3-chloro-N,N-dimethylbenzamide (52 mg, 0.262 mmol) in MeCN (520 mL). The reaction mixture was refluxed for 1 hour before being concentrated under vacuum. The residue was purified via Biotage silica gel column chromatography eluting with (cyclohexane/EtOAc 80/20 to 60/40) to afford the title product as a white solid (57 mg, 93%). 1H NMR (500 MHz, CDCl3) d 3.06 (s, 6H), 4.68 (br s, 2H), 7.34 (s, 2H). LC (Method D)-MS (ESI, m/z) tR 1.50 min, 233 [(M+H+), 100%].

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationbefore being concentrated under vacuum
  3. customThe residue was purified via Biotage silica gel column chromatography
  4. washeluting with (cyclohexane/EtOAc 80/20 to 60/40)

Sources & evidence

ORD record
ord-86027eb80ad04f2892398b18b936c358
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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