Hydrochloric Acid → HCID 13280073, compound

HRID 2164791Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=2[C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[I-:34].[K+].[OH-].[Na+]>O>[I:34][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=2[C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of 2-(4-aminobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide (11.0 g; hereinbefore prepared in Example 16) in a mixture of concentrated hydrochloric acid (9.5 ml) and water (50 ml) was cooled to between 0° C. and 5° C. whilst a solution of sodium nitrite (2.09 g) in water (15 ml) was added dropwise over 15 minutes. A solution of potassium iodide (4.58 g) in water (10 ml) was then added over 30 minutes, maintaining a temperature between 0° C. and 10° C. The mixture was then heated at 95° C. for 15 minutes. The resultant solution was cooled and adjusted to pH 8 by dropwise addition of 10% w/v aqueous sodium hydroxide solution. The solid precipitate was collected, washed with water and recrystallised from ethyl acetate to give 2-(4-iodobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide in the form of a pale-yellow solid, m.p. 162°-166° C. (yield: 3.4 g).

Workup

customhereinbefore prepared in Example 16)
additionwas added dropwise over 15 minutes
temperaturemaintaining a temperature between 0° C. and 10° C
additionadjusted to pH 8 by dropwise addition of 10%
customThe solid precipitate was collected
washwashed with water
customrecrystallised from ethyl acetate

Sources & evidence

ORD record: ord-a823988d037b465fb6d4aa8bfdca5f87
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04507315

Reaction notes

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