1-Hydroxybenzotriazole → HCID 68849646, compound

HRID 29221Notes

Reaction equation

HRID 29221 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]([NH2:11])([CH3:10])[CH3:9].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:34][C:35]1[CH:36]=[C:37]([CH:45]=[C:46]([Cl:48])[CH:47]=1)[O:38][CH:39]([CH2:43][CH3:44])[C:40](O)=[O:41]>CN(C)C=O.O.C(N(CC)CC)C>[Cl:34][C:35]1[CH:36]=[C:37]([CH:45]=[C:46]([Cl:48])[CH:47]=1)[O:38][CH:39]([CH2:43][CH3:44])[C:40]([NH:11][C:8]([CH3:10])([CH3:9])[C:7]#[C:6][CH2:5][CH2:4][CH2:3][Cl:2])=[O:41]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 130607432-(3,5-Dichlorophenoxy)butanoic acidHCID 86602731HCID 86602731, compound

Product 1

HCID 68849646HCID 68849646, compoundYield 97.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

1-Chloro-6-methylhept-4-yn-6-yl amine hydrochloride (9.8 g) in N,N-dimethylformamide (250 ml) containing triethylamine (10.4 ml) was stirred at ambient temperature for 10 minutes. The suspension which had formed was treated sequentially with 1-hydroxybenzotriazole (7.59 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.56 g) then 2-(3,5-dichlorophenoxy)-butyric acid (13.07 g) in N,N-dimethylformamide (50 ml). The mixture was stirred at ambient temperature for 2 hours, stored for 18 hours then poured into water. The product was extracted with ethyl acetate (three times). The extracts were combined, washed with a saturated aqueous solution of sodium hydrogen carbonate and water (three times) and dried over magnesium sulphate. They were then evaporated under reduced pressure to give the required product as a yellow gum (19.1 g) sufficiently pure for further derivatisation. A portion of the gum (0.33 g) was fractionated by chromatography (silica; hexane/diethyl ether, 4:1 by volume) to provide a pure sample of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide as a colourless oil, 0.22 g, 1H NMR (CDCl3) δ: 1.00-1.04(3H, t); 1.58(6H, s); 1.90-2.00(4H, m); 2.36-2.40(2H, t); 3.62-3.66(2H, t); 4.36-4.40(1H, t); 6.26(1H, s); 6.84(2H, s); 7.02(1H, s).

Workup

  1. customThe suspension which had formed
  2. stirringThe mixture was stirred at ambient temperature for 2 hours
  3. waitstored for 18 hours
  4. extractionThe product was extracted with ethyl acetate (three times)
  5. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and water (three times)
  6. dry with materialdried over magnesium sulphate
  7. customThey were then evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8ba7d7510de4c138105c7bba20d4300
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

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