Benzylamine → HCID 11268889, compound

HRID 2116746Notes

Reaction equation

HRID 2116746 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]([CH2:15][CH:16]1[CH2:18][O:17]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([N:26]1[CH2:3][CH:2]([OH:1])[CH2:4][N:5]([S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:15][CH:16]([OH:17])[CH2:18]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7504Benzylamine3×HCID 11207928N,N-bis(2-oxiranylmethyl)benzenesulfonamide

Product 1

HCID 11268889HCID 11268889, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (900 mL, 18 vol) was added to the chlorobenzene solution from step (i) above. Benzylamine (24.3 mL, 0.7 equiv.) was added in one portion (no exotherm seen) and the reaction was heated at reflux for 3 hours. More benzylamine was added (4.8 mL) and the solution was heated for a further 3 hours. More benzylamine (2.4 mL) was added and the mixture was heated at reflux for 1 hour. Ethanol (500 mL) was removed by atmospheric pressure distillation. Chlorobenzene (200 mL) was added and a further 400 mL of solvent was removed by distillation. Chlorobenzene (100 mL) was added and 150 mL of solvent was removed by reduced pressure distillation (50 mbar). The crude product (now theoretically in 250 mL of chlorobenzene) was used in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperaturethe solution was heated for a further 3 hours
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 1 hour
  6. customEthanol (500 mL) was removed by atmospheric pressure distillation
  7. additionChlorobenzene (200 mL) was added
  8. customa further 400 mL of solvent was removed by distillation
  9. additionChlorobenzene (100 mL) was added
  10. custom150 mL of solvent was removed by reduced pressure distillation (50 mbar)

Sources & evidence

ORD record
ord-930bdaf80929421891c9375fdf25c19e
Source dataset
uspto-grants-2008_10
Patent number
US07439355B2

Reaction notes

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