Hydrochloric Acid → HCID 20225351, compound

HRID 1249198Notes

Reaction equation

HRID 1249198 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1.[CH:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([BH3-])#N.[Na+].[ClH:30]>O.CO>[ClH:30].[CH2:18]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:17])[C:6]1[CH:7]=[CH:8][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:10][CH:11]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8130HeptanalHCID 5003444Sodium cyanoborohydrideHCID 14739872HCID 14739872, compound

Product 1

HCID 20225351HCID 20225351, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 1 l. of methanol is added 10.0 g (0.0389 mole) of N-(2-aminoethyl)-4-[(methylsulfonyl)amino]benzamide. The suspension is refluxed for 1 hour, then cooled. To the suspension is added 4.66 g (0.0408 mole) heptaldehyde, the mixture is then stirred over ice for 30 minutes. To the chilled mixture is added 10.26 g (0.1632 mole) of sodium cyanoborohydride. The reaction is stirred at room temperature for 24 hours, conc. HCl is added to keep the pH at about 6.0. After about 24 hours the pH of of the reaction is adjusted to pH=1.0 and reduced to 1/3 volume. 100 ml of water is added and the solid is filtered. The resultant solid is suspended in 100 ml DMF, heated to 120° C. and filtered hot. The solution is cooled and the resultant solid is filtered and dried to yield the title compound.

Workup

  1. temperatureThe suspension is refluxed for 1 hour
  2. temperaturecooled
  3. stirringThe reaction is stirred at room temperature for 24 hours
  4. waitAfter about 24 hours the pH of of the reaction is adjusted to pH=1.0
  5. filtrationthe solid is filtered
  6. filtrationfiltered hot
  7. temperatureThe solution is cooled
  8. filtrationthe resultant solid is filtered
  9. customdried

Sources & evidence

ORD record
ord-fa068da5cc0c4d81b974fe9aeb6ab961
Source dataset
uspto-grants-1986_12
Patent number
US04629739

Reaction notes

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