Sodium Hydroxide → 5-Chloro-thiophene-2-carboxylic acid (5-imidazol-1-yl-pentyl)-amide

HRID 1154338Notes

Reaction equation

HRID 1154338 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](Cl)=[O:8])=[CH:4][CH:3]=1.[N:10]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:14]=[CH:13][N:12]=[CH:11]1.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 71384341H-Imidazole-1-pentanamine

Product 1

HCID 133710945-Chloro-thiophene-2-carboxylic acid (5-imidazol-1-yl-pentyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.8 g. of 5-chlorothiophene-2-carbonyl chloride in 10 ml. of CH2Cl2 was added to a mixture of 1.52 g. of 1H-imidazole-1-pentanamine, 10 ml. of 1N NaOH and 50 ml. of CH2Cl2. The reaction mixture was stirred for 20 hours and then treated with 25 ml. of CH2Cl2 and 5 ml. of 1N NaOH. The layers were separated and the organic layer was washed with water, dried over MgSO4 and concentrated. The crystalline residue was washed with diethyl ether whereby the desired product, m.p. 123°-125° C., was obtained.

Workup

  1. additiontreated with 25 ml
  2. customThe layers were separated
  3. washthe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washThe crystalline residue was washed with diethyl ether whereby the desired product, m.p. 123°-125° C.
  7. customwas obtained

Sources & evidence

ORD record
ord-4a20de1c3f91462891dcfb896e1d31bd
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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