Dichloromethane → HCID 19736873, compound

HRID 326402Notes

Reaction equation

HRID 326402 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-3c0f7cc247174b7880ca9d92ceb855af
Source dataset
uspto-grants-1993_12
Patent number
US05268468

Reaction notes

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