Benzylamine → HCID 20029768, compound

HRID 1721966Notes

Reaction equation

HRID 1721966 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH2:22][CH2:23][CH2:24][CH3:25])(=[O:21])=[O:20])=[CH:14][CH:13]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[C:27]1([CH2:26][NH:33][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH2:22][CH2:23][CH2:24][CH3:25])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 20029785HCID 20029785, compound

Product 1

HCID 20029768HCID 20029768, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of stage (ii) (0.85 g) was added dropwise over 5 min to stirred benzylamine (1.17 g) at 120° under nitrogen. The solution was stirred at 120° under nitrogen for 2 h, cooled and diluted with dichloromethane (100 ml). The mixture was washed with 2N hydrochloric acid (40 ml), the aqueous phase was re-extracted with further dichloromethane (2×40 ml), and the combined organic extracts were washed with 8% sodium bicarbonate solution (80 ml), dried and evaporated in vacuo to give the title compound as a yellow oil (0.5 g). T.l.c. (System C 39:10:2) Rf 0.49.

Workup

  1. temperaturecooled
  2. washThe mixture was washed with 2N hydrochloric acid (40 ml)
  3. extractionthe aqueous phase was re-extracted with further dichloromethane (2×40 ml)
  4. washthe combined organic extracts were washed with 8% sodium bicarbonate solution (80 ml)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-891583bde5904810a66d231f6f29ae21
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Reaction notes

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