1,3-Dioxolane-2-ethylamine → 4,5-Dibromo-N-[2-(1,3-dioxolan-2-yl)ethyl]pyrrole-2-carboxamide

HRID 1860238Notes

Reaction equation

HRID 1860238 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.ClC([C:13]([C:15]1[NH:16][C:17]([Br:21])=[C:18]([Br:20])[CH:19]=1)=[O:14])(Cl)Cl>C(#N)C>[Br:20][C:18]1[CH:19]=[C:15]([C:13]([NH:1][CH2:2][CH2:3][CH:4]2[O:8][CH2:7][CH2:6][O:5]2)=[O:14])[NH:16][C:17]=1[Br:21]

Participants

4

Reactant 2

HCID 798271,3-Dioxolane-2-ethylamineHCID 27633462,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethan-1-one

Product 1

HCID 110899034,5-Dibromo-N-[2-(1,3-dioxolan-2-yl)ethyl]pyrrole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2-aminoethyl)-1,3-dioxolane (2.4 g, 20.6 mmol) and 4,5-dibromopyrrol-2-yl trichloromethyl ketone (7.6 g, 20.5 mmol) in 30 mL of acetonitrile was stirred at room temperature for 16 h. The reaction mixture was filtered and the precipitate 11 (6.8 g, 90%) was collected as a colorless solid: mp 155-157° C.; 1H NMR (CDCl3) d 1.99 (dt, 2H, J=6.0, 4.2), 3.61 (dt, 2H, J=6.0, 5.6), 3.92 (m, 2H), 4.05 (m, 2H), 5.00 (t, 1H, J=4.2), 6.51 (d, 1H, J=2.8), 6.66 (bs, 1H), 10.57 (bs, 1H); 13C NMR (CD3COCD3) d 34.3 (e), 35.5 (e), 65.4×2 (e), 99.4 (e), 103.4 (o), 105.4 (e), 113.0 (o), 129.1 (e), 160.0 (e); IR (nujol) 3358, 1646, 1569, 1412, 1372 cm−1; UV (CH3OH) lmax 275, 233, 214 (sh) nm; MS m/z (relative intensity) 371 (M++5, 50), 369 (M++3, 100), 367 (M++1, 50), 289 (13), 118 (25), 101 (50), 73 (30); Anal. Calcd for C8H10N2O2Br2: C, 32.63; H, 3.29; N, 7.61; Found: C, 32.77; H, 3.17; N, 7.51.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe precipitate 11 (6.8 g, 90%) was collected as a colorless solid

Sources & evidence

ORD record
ord-cd5f971b152f4bdc9c5e011da7f7f9ed
Source dataset
uspto-grants-2003_03
Patent number
US06528646B2

Reaction notes

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