Hydrochloric Acid → 1-(2-Iodophenyl)cyclopropanecarboxamide

HRID 592350ノート

反応式

HRID 592350 の反応式
C1C=CC2N(O)N=[N:7]C=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[I:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1([C:34]([OH:36])=O)[CH2:33][CH2:32]1.CCN(CC)CC.C(=O)([O-])[O-].[NH4+].[NH4+]>CN(C=O)C.C1COCC1>[I:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1([C:34]([NH2:7])=[O:36])[CH2:33][CH2:32]1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 200261901-(2-Iodophenyl)cyclopropane-1-carboxylic acid

生成物 1

HCID 867122741-(2-Iodophenyl)cyclopropanecarboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

HOBt (1.89 g, 14.0 mmol) and EDCl.HCl (2.69 g, 14.0 mmol) were added to a solution of 1-(2-iodophenyl)cyclopropanecarboxylic acid (I10) (3.11 g, 10.8 mmol) in DMF (6 mL), THF (29 mL) and Et3N (9.4 mL, 54 mmol). After 15 minutes ammonium carbonate (7.95 g, 86.4 mmol) was added and the resulting mixture was stirred at room temperature for 20 hours. The volatiles were removed in vacuo and water (150 mL) was added to the residue resulting in the formation of a suspension. The suspension was sonicated for several minutes, filtered and the filter cake dried to give the title compound I11 as an off white solid (2.55 g, 82%); 1H NMR (300 MHz, d6-DMSO) δ 7.87 (d, J=7.6 Hz, 1H), 7.36-7.38 (m, 2H), 7.02-7.08 (m, 1H), 6.96 (brs, 1H), 6.05 (brs, 1H), 1.52 (brs, 2H), 0.96 (brs, 2H). LCMS-B: rt 5.800 min; m/z 288 [M+H]+.

後処理

  1. customThe volatiles were removed in vacuo and water (150 mL)
  2. additionwas added to the residue
  3. customresulting in the formation of a suspension
  4. customThe suspension was sonicated for several minutes
  5. filtrationfiltered
  6. customthe filter cake dried

出典と根拠

ORDレコード
ord-91cd16fb2a3a49d3b6c03516463ad12b
出典データセット
uspto-grants-2016_01
特許番号
US09238644B2

反応ノート

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