Aniline → HCID 8190068, compound

HRID 239810Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:10]=[C:11]([S:15]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a 30 gallon (˜136 L) reactor was charged aniline (2) (4.01 kg; 93.13 g/mol; 43 mol), toluene (25 L), and 4-(dimethylamino)pyridine (DMAP) (12 g), and the mixture was heated to 50-60° C. 3-Bromobenzenesulfonyl chloride (1) (5 kg; 255.52 g/mol; 19.6 mol) was charged into the reactor over 30 minutes at 50-60° C. and progress of the reaction was monitored by HPLC. After 19 hours, toluene (5 L) was added due to losses overnight through the vent line and the reaction was deemed to be complete with no compound (1) being detected by HPLC. The reaction mixture was diluted with toluene (10 L) and then quenched with 2 M aqueous hydrochloric acid (20 L). The organic and aqueous layers were separated, the aqueous layer was discarded, and the organic layer was washed with water (20 L), and then 5% (w/w) sodium bicarbonate solution (20 L), while maintaining the batch temperature at 45-55° C. The batch was then used in the next synthesis.

Workup

customquenched with 2 M aqueous hydrochloric acid (20 L)
customThe organic and aqueous layers were separated
washthe organic layer was washed with water (20 L)
temperature5% (w/w) sodium bicarbonate solution (20 L), while maintaining the batch temperature at 45-55° C
customThe batch was then used in the next synthesis

Sources & evidence

ORD record: ord-b740f7e2eb674fc4a157bc5f94da3ff3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642809B2

Reaction notes

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