Dichloromethane → HCID 19759044, compound

HRID 1586691Notes

Reaction equation

HRID 1586691 reaction equation
ClCCl.[OH-].[Na+].Cl.[CH3:7][NH:8][OH:9].[Br:10][CH:11]([CH2:15][CH2:16]Br)[C:12](Cl)=[O:13]>O>[Br:10][CH:11]1[CH2:15][CH2:16][O:9][N:8]([CH3:7])[C:12]1=[O:13]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium Hydroxide3×HCID 77906N-methylhydroxylamine hydrochlorideHCID 44131432,4-Dibromobutyryl chloride

Product 1

HCID 19759044HCID 19759044, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 65 mL of dichloromethane and 2.6 g (33 mmol) of 50% aqueous sodium hydroxide in 8 mL of water was treated with 2.5 g (30 mmol) of N-methylhydroxylamine hydrochloride. After cooling to 5° C., 8.5 g (32 mmol) of 2,4-dibromobutyryl chloride* was added dropwise, with the temperature maintained at 5° to 8° C. An additional 2.6 g of 50% aqueous sodium hydroxide was added, and the mixture was stirred for 2 hours at 5° C. A final 2.6 g of 50% aqueous sodium hydroxide was added, and the mixture was stirred at room temperature for 18 hours. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried (anhydrous magnesium sulfate) and evaporated.

Workup

  1. temperaturemaintained at 5° to 8° C
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried (anhydrous magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-21fb7b96d0d545bbb0dbe7d8dfc5d6a1
Source dataset
uspto-grants-1993_06
Patent number
US05215986

Reaction notes

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