Hydrochloric Acid → HCID 53942266, compound

HRID 1587539Notes

Reaction equation

HRID 1587539 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[CH3:20][S:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.[C:30]([BH3-])#[N:31].[Na+].Cl>CO.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C(O)C>[CH3:20][S:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:31][CH2:30][C:25]2[CH:28]=[CH:29][C:22]([S:21][CH3:20])=[CH:23][CH:24]=2)=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 769854-(Methylthio)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 14791311HCID 14791311, compound

Product 1

HCID 53942266HCID 53942266, compound

Reagents, catalysts & solvents 3

HCID 6451Bromocresol GreenCatalystHCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

Dissolve 1,6,14,19-tetraazanonadecane (1.35 g, 0.005 mol) in methanol (distilled from Mg) (50 mL) and add 4-(methylthio)benzaldehyde (1.52 g, 0.01 mol), sodium cyanoborohydride (0.62 g, 0.010 mol) and 1 drop of 1% bromocresol green in ethanol. Maintain the pH of the reaction with 1N hydrochloric acid in methanol until the indicator no longer changes. Evaporate the solvent in vacuo and partition the residue between 1N sodium hydroxide (50 mL) and ethyl acetate (100 mL). Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo give the title compound.

Workup

  1. temperatureMaintain
  2. customEvaporate the solvent in vacuo
  3. custompartition the residue between 1N sodium hydroxide (50 mL) and ethyl acetate (100 mL)
  4. customSeparate the organic phase
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-788d487b77364d9e983e5cdad1d210e6
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

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