Potassium Carbonate → HCID 19955417, compound

HRID 1779338Notes

Reaction equation

HRID 1779338 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.Cl.Cl[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:1]1([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]3)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 522769Bis(2-chloroethyl)amine hydrochloride2×HCID 19955413HCID 19955413, compound

Product 1

HCID 19955417HCID 19955417, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the product of Example 3 (9.5 g, 0.051 mol), bis(2-chloroethyl)amine hydrochloride (10.6 g, 0.06 mol), and potassium carbonate (8.3 g, 0.06 mol) in anhydrous dimethylformamide (30 ml) was heated at 110° C. under argon. Further addition of bis(2- chloroethyl)amine hydrochloride (5.5 g. 0.031 mol) and potassium carbonate (4.2 g, 0.031 mol) were made after 7 h and 16 h. After another 6 h,the reaction mixture was poured into dilute potassium carbonate solution (400 ml) and extracted with ether (3×300 ml) and ethyl acetate (2×250 ml). The extracts were combined, dried (MgSO4), and washed with water (2×200 ml). Evaporation of the solvent in vacuo gave a solid which was recrystallised from ether to give the product (5.0 g) as off-white crystals, m.p. 177°-180° C.

Workup

  1. waitAfter another 6 h
  2. extractionextracted with ether (3×300 ml) and ethyl acetate (2×250 ml)
  3. dry with materialdried (MgSO4)
  4. washwashed with water (2×200 ml)
  5. customEvaporation of the solvent in vacuo
  6. customgave a solid which
  7. customwas recrystallised from ether

Sources & evidence

ORD record
ord-b3b9655662e34ac2970888bd582913db
Source dataset
uspto-grants-1997_05
Patent number
US05627177

Reaction notes

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