Dichloromethane → HCID 19875836, compound

HRID 1886345Notes

Reaction equation

HRID 1886345 reaction equation
O[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1)[CH:3]([CH3:5])[CH3:4].[Cl:19]CCl.CS(Cl)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.C(N(CC)CC)C>[Cl:19][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1)[CH:3]([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 19875845HCID 19875845, compound

Product 1

HCID 19875836HCID 19875836, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 36 parts of intermediate 15, namely N-[4-(1-hydroxy-2-methylpropyl)-2-nitrophenyl]acetamide and 390 parts of dichloromethane were added 35.0 parts of N,N-diethylethanamine. After cooling to 0° C., 20.0 parts of methanesulfonyl chloride were added dropwise to the previous mixture. Upon completion, stirring was continued for 12 hours at room temperature. The whole was poured into water and sodium carbonate was added while stirring. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 39 parts (100%) of N-[4-(1-chloro-2-methylpropyl)-2-nitrophenyl]acetamide (interm. 16).

Workup

  1. additionwas added
  2. stirringwhile stirring
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9094aa29297946088d0876be37701e8a
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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