Nitrogen mustard hydrochloride → HCID 9823477, compound

HRID 2116785Notes

Reaction equation

HRID 2116785 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=1)=[O:12])[CH2:6]2.Cl.[CH3:27][N:28]([CH2:32][CH2:33]Cl)[CH2:29][CH2:30]Cl.C(=O)([O-])O.[Na+]>C(O)CCC>[CH3:27][N:28]1[CH2:32][CH2:33][N:1]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH:5]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=2)=[O:12])[CH2:6]3)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 516892Sodium BicarbonateHCID 10903842HCID 10903842, compound

Product 1

HCID 9823477HCID 9823477, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-amino-N-(4-morpholinophenyl)indan-2-carboxamide (1.1 g, 3 mmol), N-methyl-bis-(2-chloroethyl)amine hydrochloride (2.0 g, 10 mmol) and sodium hydrogen carbonate (8.0 g, 95 mmol) in 1-butanol (100 mL) was stirred overnight at 120° C. The mixture was filtered and the solvent was evaporated in vacuo. The crude residue (oil) was purified on a silica gel column using methylene chloride as the eluent to afford 100 mg of the title compound: mp 248-249° C.; EIMS (70 eV) m/z (relative intensity) 420 (47, M+).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated in vacuo
  3. customThe crude residue (oil) was purified on a silica gel column

Sources & evidence

ORD record
ord-0abe92f23af04eccb1675cce18abccc8
Source dataset
uspto-grants-2008_10
Patent number
US07439356B2

Reaction notes

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