Benzylamine → HCID 14157963, compound

HRID 2398718Notes

Reaction equation

HRID 2398718 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[N:24]=[C:25]=[S:26])(=[O:3])[CH3:2].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C(C)=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH:24][C:25]([NH:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[S:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 12899825HCID 12899825, compound

Product 1

HCID 14157963HCID 14157963, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 10 ml of anhydrous xylene were added 390 mg (1 mmol) of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl isothiocyanate and then slowly added 110 mg (1 mmol) of benzylamine (MW 107) under ice-cooling and stirring over 30 minutes. The mixture was then stirred at room temperature for 1.5 hours, during which crystals were deposited and then filtered off. Recrystallization from ethanol gave colourless needles melting between 126° and 128° C. (uncorrected). Yield: 198 mg (40%).

Workup

  1. stirringThe mixture was then stirred at room temperature for 1.5 hours, during which crystals
  2. filtrationfiltered off
  3. customRecrystallization from ethanol
  4. customgave colourless needles
  5. custommelting between 126° and 128° C.

Sources & evidence

ORD record
ord-2e460e373eca4cf29e95dbbf80b1ee67
Source dataset
uspto-grants-1977_05
Patent number
US04025622

Reaction notes

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