Butyryl chloride → HCID 67105835, compound

HRID 2357117Notes

Reaction equation

HRID 2357117 reaction equation
[Cl-].[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:13]2[N:14]=[CH:15][NH2+:16][CH:17]=2)=[CH:5][CH:4]=1.[C:18]([Cl:23])(=[O:22])[CH2:19][CH2:20][CH3:21]>C(O)(C(F)(F)F)=O>[Cl-:23].[C:18]([O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:13]2[N:14]=[CH:15][NH2+:16][CH:17]=2)=[CH:5][CH:4]=1)(=[O:22])[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 178515463HCID 178515463, compound

Product 1

HCID 67105835HCID 67105835, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(6-hydroxy-indan-1-ylmethyl)-1H-imidazol-1-ium chloride (100 mg, 0.399 mmol) and butyric acid chloride (510 mmol) were reacted in TFA (1 ml) and purified as described in example 1. Yield 90 mg (77%) of a white hygroscopic solid. 1H NMR (CDCl3, TMS): δ 1.02 (t, 3H), 1.70-1.79 (m, 3H), 2.18-2.24 (m, 1H), 2.52 (t, 2H), 2.73-2.86 (m, 3H), 3.18 (dd, 1H), 3.53 (qui, 1H), 6.84 (dd, 1H), 6.87 (s, 1H), 6.92 (s, 1H), 8.66 (s, 1H), 11.28 (s (broad), 2H). 13C NMR (CDCl3, TMS): δ 13.66, 18.45, 29.68, 30.52, 31.68, 36.24, 43.98, 115.79, 117.05, 120.36, 125.36, 132.32, 132.59, 141.32, 146.36, 149.51, 172.85.-HPLC-MS (EI): m/z=285.2 ((M+H)+—Cl−). Anal.—Calc. for C17H20N2O2.HCl.0.2CH2Cl2: C, 61.16; H, 6.39; N, 8.29. Found C, 61.30; H, 6.46; N, 8.22.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-39065c50db5345b1b81ef28d9132c45f
Source dataset
uspto-grants-2010_07
Patent number
US07759496B2

Reaction notes

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