4-Iodobenzoyl chloride → HCID 53700093, compound

HRID 610641Notes

Reaction equation

HRID 610641 reaction equation
[H+].[CH3:2][C@H:3]([NH2:12])[C@H:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[I:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>C(Cl)Cl.[OH-].[Na+]>[I:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:12][CH:3]([CH3:2])[CH:4]([OH:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 498534023198-15-0

Product 1

HCID 53700093HCID 53700093, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a ice-cooled mixture of norephedrine hydrochloride (1) (7.02 g, 37.5 mmol) in CH2Cl2 (180 mL) and 5% NaOH aqueous solution (60 mL) was added dropwise a solution of 4-Iodobenzoyl chloride (2c, 10.1 g, 37.9 mmol) in CH2Cl2 (100 mL). After the addition had completed, the resulting mixture was stirred at 0° C. for 4 h. The solvent was removed in vacuo. The residue was washed with H2O, dried, the recrystallized from EtOH to provide a white solid (12.8 g, 90%). mp 209-210° C. 1H NMR (DMSO-d6) d 1.03 (d, J=6.6 Hz, 3 H, CH3), 4.05-4.12 (m, 1 H, --CHCH3), 4.65 (s, 1 H, --CHOH), 5.46 (d, J=3.6 Hz, 1 H, NH), 7.14 (t, J=7.2 Hz, 1 H, aromatic), 7.23 (t, J=7.5 Hz, 2 H, aromatic), 7.32 (d, J=7.2 Hz, 2 H, aromatic), 7.53 (d, J=8.4 Hz, 2 H, aromatic), 7.75 (d, J=8.1 Hz, 2 H, aromatic), 8.30 (d, J=8.4 Hz, 1 H, aromatic). 13C NMR (DMSO-d6) d 14.70 (q, CH3), 51.30 (d, --CHCH3), 74.41 (d, --CHOH), 98.48 (s, =CI--, aromatic), 126.23 (d, aromatic), 126.73 (d, aromatic), 127.75 (d, aromatic), 129.29 (d, aromatic), 134.19 (s, aromatic), 137.03 (d, aromatic), 143.59 (s, aromatic), 164.70 (s, aromatic). Anal. Calcd. for C16H16INO2 : C, 50.41; H, 4.23; N, 3.67. Found: C, 50.35; H, 4.24; N, 3.65.

Workup

  1. additionAfter the addition
  2. customThe solvent was removed in vacuo
  3. washThe residue was washed with H2O
  4. customdried
  5. customthe recrystallized from EtOH

Sources & evidence

ORD record
ord-a42b4cf021234e13aeef2ce0fbbc91cc
Source dataset
uspto-grants-1999_12
Patent number
US05998624

Reaction notes

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