Sodium Hydroxide → HCID 67693808, compound

HRID 1417333Notes

Reaction equation

HRID 1417333 reaction equation
Cl.Cl.[N:3]1([C:8]2[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.[OH-].[Na+].[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:16][CH2:15][CH2:14][CH2:13][O:12][C:11]2[CH:17]=[CH:18][C:8]([N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)=[CH:9][CH:10]=2)=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 685154-Bromobenzoyl chlorideHCID 67598526HCID 67598526, compound

Product 1

HCID 67693808HCID 67693808, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.04 g of 3-[4-(1H-imidazol-1-yl)phenoxy]propanamine dihydrochloride (Example 92) in 70 ml of methylene chloride is treated with 21 ml of 1N NaOH followed by 1.54 g of 4-bromobenzoyl chloride with stirring at room temperature for 18 hours. Additional methylene chloride and 5 ml of 1N NaOH is added and the organic layer separated, washed with water and filtered. The organic layer is evaporated in vacuo to a residue which is washed with ether and dried to give 1.3 g of off-white solid, m.p. 183°-185° C.

Workup

  1. customthe organic layer separated
  2. washwashed with water
  3. filtrationfiltered
  4. customThe organic layer is evaporated in vacuo to a residue which
  5. washis washed with ether
  6. customdried

Sources & evidence

ORD record
ord-50d2d58aea184c1482a2ccbaab40eaab
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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