Dimethylformamide → HCID 69654567, compound

HRID 1795370Notes

Reaction equation

HRID 1795370 reaction equation
[H-].[Na+].[S:3]1(=[O:17])(=[O:16])[C:8]2=[CH:9][CH:10]=[CH:11][C:12]3=[CH:13][CH:14]=[CH:15][C:6](=[C:7]23)NC1.Cl.[CH2:19]([N:21]([CH2:24]CCl)[CH2:22]C)[CH3:20].[CH3:27][N:28](C)C=O>>[O:17]=[S:3]1(=[O:16])[C:8]2=[CH:9][CH:10]=[CH:11][C:12]3=[CH:13][CH:14]=[CH:15][C:6](=[C:7]23)[CH2:27][N:28]1[CH2:20][CH2:19][N:21]([CH3:24])[CH3:22]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 22217720HCID 22217720, compound

Product 1

HCID 69654567HCID 69654567, compound

Procedure

0.028 g of sodium hydride is suspended in 0.5 mL of dimethylformamide and 0.073 g of 2,3-dihydro-naphtho[1,8-de][1,3]thiazine-1,1-dioxide in 1 mL of dimethylformamide is added. Then 0.053 g of diethylaminoethyl chloride-hydrochloride are added batchwise. The reaction mixture is stirred for 18 hours at ambient temperature and then poured onto ice water. The mixture is extracted with dichloromethane and the organic extracts collected are dried with sodium sulfate. After evaporation in vacuo, the residue obtained is purified by chromatography. Yield: 0.035 g; m.p.: 97° C.–98° C.

Workup

  1. additionpoured onto ice water
  2. extractionThe mixture is extracted with dichloromethane
  3. customthe organic extracts collected
  4. dry with materialare dried with sodium sulfate
  5. customAfter evaporation in vacuo
  6. customthe residue obtained
  7. customis purified by chromatography

Sources & evidence

ORD record
ord-bba18c74ab6e4c90b46e68766205183a
Source dataset
uspto-grants-2006_04
Patent number
US07026475B2

Reaction notes

Loading…