Dimethylcarbamoyl Chloride → HCID 10223410, compound

HRID 393172Notes

Reaction equation

HRID 393172 reaction equation
[H-].[K+].[C:3]1([CH:13]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][N:17]3[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[S:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>C1COCC1>[CH3:28][N:29]([CH3:33])[C:30]([O:20][C:19]1[C:18]2=[CH:21][CH:22]=[CH:23][N:17]2[C:16]2[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=2[S:14][C:13]=1[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)=[O:31]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82127Potassium hydrideHCID 11152016HCID 11152016, compound

Product 1

HCID 10223410HCID 10223410, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium hydride (0.167 g, 1.46 mmol, 35% in oil) in anhydrous THF (4.0 mL) was added the the (±)-6-(1-naphthyl)pyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one (500 mg, 1.46 mmol) dissolved in anhydrous THF (5 mL). The reaction mixture was stirred at rt for 2 h, and then dimethylcarbamoyl chloride (0.181 g, 1.68 mmol) was slowly added. After stirring for 8 h at 30° C., the solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic layer was washed with brine, dried and concentrated. The residue was chromatographed (dichloromethane) to give the PBOX-8 in 82% yield. IR (neat) 1725 cm−1; 1HNMR (CDCl3) δ 2.43 (s, 3 H), 2.58 (s, 3 H), 6.45 (m, 1 H), 6.64 (m, 1 H), 7.18-7.57 (m, 10 H), 7.77-7.86 (m, 2 H).

Workup

  1. stirringAfter stirring for 8 h at 30° C.
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed (dichloromethane)
  8. customto give the PBOX-8 in 82% yield

Sources & evidence

ORD record
ord-26bc91c3879947949bfce2efe3998033
Source dataset
uspto-grants-2004_10
Patent number
US06806267B1

Reaction notes

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