Succinic anhydride → HCID 86758459, compound

HRID 2304368Notes

Reaction equation

HRID 2304368 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Cl:8][CH2:9][CH2:10][N:11]([CH2:19][CH2:20][Cl:21])[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:8][CH2:9][CH2:10][N:11]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[CH:16][CH:17]=1)[CH2:19][CH2:20][Cl:21]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 71000Hydroxyaniline mustard2×

Product 1

HCID 86758459HCID 86758459, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of succinic anhydride (225 mg, 2.25 mmol) in CHCl3 (10 ml) was added under stirring, 4-[N,N-bis(2-chloroethyl)-amino]phenol (compound 6, FIG. 7; 203 mg, 0.75 mmol) followed by triethylamine (75 mg, 0.75 mmol). The mixture was stirred overnight and the solvent evaporated. The crude residue was dissolved in EtOAC/Et2O/H2O and under stirring the pH was adjusted to 3. The organic layer was washed with water, brine, dried (MgSO4), and evaporated. The resulting oil was crystallised from Et2O/hexane and the white solid was filtered off and dried under vacuum to obtain the desired end product (210 mg; yield 83%). Melting point 98-100° C.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred overnight
  3. customthe solvent evaporated
  4. dissolutionThe crude residue was dissolved in EtOAC/Et2O/H2O
  5. stirringunder stirring the pH
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe resulting oil was crystallised from Et2O/hexane
  10. filtrationthe white solid was filtered off
  11. customdried under vacuum
  12. customto obtain the desired end product (210 mg; yield 83%)

Sources & evidence

ORD record
ord-a9a030a72b8048f7a5cab87c596b41be
Source dataset
uspto-grants-2002_08
Patent number
US06436691B1

Reaction notes

Loading…