Diisopropylethylamine → HCID 67129270, compound

HRID 2201720Notes

Reaction equation

HRID 2201720 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][Br:19])=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5211735-Bromovaleryl chlorideHCID 11253521Benzyl N-(4-aminophenyl)carbamate

Product 1

HCID 67129270HCID 67129270, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aniline 1 (12.69 g, 0.052 mol) was stirred in dichloromethane at 0° C. and 5-bromovaleryl chloride (8.9 mL, 0.052 mol) added followed by diisopropylethylamine (9 mL, 0.052 mol). The resulting white suspension was allowed to warm to room temperature and stirred for 3 h. The white solid was collected by filtration and recrystallised from ethyl acetate to give 2 as a white fluffy powder (10.22 g, 50%).

Workup

  1. filtrationThe white solid was collected by filtration
  2. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f061b44e73534e80bf7c93964b421c72
Source dataset
uspto-grants-2016_06
Patent number
US09365508B2

Reaction notes

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