Dichloromethane → HCID 22096808, compound

HRID 1458700Notes

Reaction equation

HRID 1458700 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[N:17]([CH2:21]CO)[CH2:18][CH2:19]O)[C:10]([O:12][CH3:13])=[O:11].[CH2:24]([Cl:26])Cl>>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[N:17]([CH2:21][CH2:24][Cl:26])[CH2:18][CH2:19][Cl:3])[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 22096732HCID 22096732, compound

Product 1

HCID 22096808HCID 22096808, compoundYield 88%

Procedure

Thionyl chloride (0.7 ml; 9.6 mmol) was added to a solution of 1.0 g (3.7 mmol) of methyl 3-methoxy-4-[bis(2-hydroxyethyl)amino]benzoate in 20 ml of methylene chloride, followed by stirring at room temperature for 3 hours. After the solvent was distilled out under reduced pressure, methylene chloride was added again in a small amount and was then distilled out under reduced pressure. This procedure was repeated twice. The resultant mixture was evaporated to dryness under reduced pressure, whereby 1.0 g of a brown oil was obtained (yield: 88%).

Workup

  1. distillationAfter the solvent was distilled out under reduced pressure, methylene chloride
  2. additionwas added again in a small amount
  3. distillationwas then distilled out under reduced pressure
  4. customThe resultant mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b658b274e71a402283e62ac0b833e2e1
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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