Dichloromethane → HCID 19736873, compound

HRID 484116Notes

Reaction equation

HRID 484116 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH:11]=1.ClCCl>O.Cl>[CH3:5][N:6]([N:1]=[O:3])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 19736880HCID 19736880, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19736873HCID 19736873, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (7.2 g) in water (50 ml) was added slowly to a solution of N-methyl-3-[4-(trifluoromethyl)phenoxy]benzenepropanamine (30 g) and dichloromethane (100 ml) in 10% hydrochloric acid (200 ml). After one hr, the reaction mixture was separated, and the aqueous phase was extracted with dichloromethane. The organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was chromatographed on silica (eluted with 50% hexanes-dichloromethane). The appropriate fractions were collected and evaporated to give 28 g (95.4%) of product, mp 75°-76° C. Recrystallization from hexanes gave the analytical sample, mp 76°-77° C.

Workup

  1. customthe reaction mixture was separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. customThe residue was chromatographed on silica (eluted with 50% hexanes-dichloromethane)
  7. customThe appropriate fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-d0bb4411652844e98b0479a8efc5c977
Source dataset
uspto-grants-1993_07
Patent number
US05229417

Reaction notes

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