Nitrogen → HCID 54555949, compound

HRID 2413628Notes

Reaction equation

HRID 2413628 reaction equation
N#N.[Cl:3][C:4]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=O)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[CH:9]2.[NH2:20][C:21]([CH3:26])([CH2:24][OH:25])[CH2:22][OH:23].O.C1(C)C=C[C:31]([S:34](O)(=[O:36])=[O:35])=CC=1.[BH4-].[Na+].[OH-].[Na+].CS(O)(=O)=O>CO.O.C1(C)C=CC=CC=1>[CH3:31][S:34]([O:23][CH2:22][C:21]([NH:20][CH2:18][C:11]1[C:10]2[C:5]([C:4]([Cl:3])=[C:17]3[C:12]=1[CH:13]=[CH:14][CH:15]=[CH:16]3)=[CH:6][CH:7]=[CH:8][CH:9]=2)([CH3:26])[CH2:24][OH:25])(=[O:36])=[O:35]

Participants

11

Reactant 7

HCID 947NitrogenHCID 15312-Amino-2-methyl-1,3-propanediolHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 8270310-Chloro-9-anthraldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

Product 1

HCID 54555949HCID 54555949, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, condenser, Dean-Stark trap and N2 bubbler was added 10-chloroanthracene-9-carbaldehyde (Aldrich, 50.0 g, 0.208 mol, 2-amino-2-methyl-1,3-propanediol (Aldrich, 43.7 g, 0.415 mol) p-toluenesulfonic acid monohydrate (Aldrich, 3.98 g, 20.8 mmol) and PhCH3 (750 mL). The mixture was refluxed for 3.5 h with azeotropic removal of H2O. Most of the PhCH3 was then distilled from the mixture. The mixture was then cooled to 0° and diluted with abs. EtOH (700 mL). Solid NaBH4 (MCB Manufacturing Chemists Inc. 2909 Highland Ave., Cincinnati, OH, 45212, 9.55 g, 0.252 mol) was then added to the reaction mixture in 0.5 g portions. The reaction was then allowed to warm to RT and stirred overnight. A 1N NaOH solution (10 mL) was then added to the reaction mixture and the solvents removed by rotary evaporation. The solid was then shaken with several portions of 1N NaOH solution (4×300 mL) and filtered. The yellow solid was washed with H2O (3×500 mL) and sucked semidry. The solid was then dissolved in a mixture of CH3OH (800 mL) and CH3SO3H (Aldrich, 19.3 g, 0.20 mol, 13.0 mL) filtered and diluted to 2.5 L with Et2O. Two further crystallizations gave 2-(((10-chloro-9-anthracenyl)methyl)amino)-2-methyl-1,3-propanediol methanesulfonate mp 234°-235° (dec.), (CH3OH/Et2O), (C, H, Cl, N, S).

Workup

  1. customTo a RB flask equipped with magnetic stirring bar, condenser
  2. distillationMost of the PhCH3 was then distilled from the mixture
  3. temperatureThe mixture was then cooled to 0°
  4. additiondiluted with abs
  5. customthe solvents removed by rotary evaporation
  6. stirringThe solid was then shaken with several portions of 1N NaOH solution (4×300 mL)
  7. filtrationfiltered
  8. washThe yellow solid was washed with H2O (3×500 mL)
  9. filtrationfiltered
  10. additiondiluted to 2.5 L with Et2O
  11. customTwo further crystallizations

Sources & evidence

ORD record
ord-5e1edf58fe5d4dd69ef58efa89ea4ea2
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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