2-Iodobenzoyl chloride → HCID 54110010, compound

HRID 610639Notes

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][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C(Cl)Cl.[OH-].[Na+]>[I:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH:12][CH:3]([CH3:2])[CH:4]([OH:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a ice-cooled mixture of norephedrine hydrochloride (1) (5.2 g, 27.8 mmol) in CH2Cl2 (120 mL) and 5% NaOH aqueous solution (40 mL) was added dropwise a solution of 2-Iodobenzoyl chloride (2a, 7.5 g, 28.1 mmol) in CH2CL2 (15 mL). The resulting mixture was stirred at 0° C. for 4 h. The solvent was removed in vacuo. The residue was washed with H2O, then dried, and recrystallized from EtOH to afford a white solid (9.5 g, 90%). mp 129-130° C. 1H NMR (CDCl3) d 1.06 (d, J=6.9 Hz, 3 H, CH3), 3.58 (bs, 1H, --CHCH3), 4.95 (d, J=2.7 Hz, 1 H, --CHOH), 6.19 (d, J=8.4 Hz, 1 H, NH), 7.01-7.06 (m, 1 H, aromatic), 7.2-7.39 (m, 7 H, aromatic), 7.77 (d, J=7.8 Hz, 1 H, aromatic). 13C NMR (CDCl3) d 13.74 (q, CH3), 51.55 (d, --CHCH3), 75.64 (d, --CHOH), 92.44 (s, =CI--, aromatic), 126.02 (d, aromatic), 126.13 (d, aromatic), 127.45 (d, aromatic), 128.07 (d, aromatic), 128.17 (d, aromatic), 139.70 (d, aromatic), 140.66 (s, aromatic), 141.85 (s, aromatic), 169.57 (s, --CONH--). Anal. Calcd. for C16H16INO2 : C, 50.41; H, 4.23; N, 3.67. Found: C, 50.25; H, 4.18; N, 3.58.

Workup

customThe solvent was removed in vacuo
washThe residue was washed with H2O
customdried
customrecrystallized from EtOH

Sources & evidence

ORD record: ord-95531616ce0d4b008e22df1281a35e0e
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998624

Reaction notes

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