Stannous chloride dihydrate → [4-(4-Fluorophenyl)sulfanylphenyl]hydrazine hydrochloride

HRID 510151Notes

Reaction equation

[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.O.O.[Sn](Cl)[Cl:23]>O.Cl>[ClH:23].[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:19]=[CH:18][C:16]([NH:17][NH2:1])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of sodium nitrite (5.90 g, 86 mmol) in water (110 mL) is added drop wise to a pre-cooled (−10° C.) slurry of 4-(4-fluorophenyl)sulfanylaniline (14.39 g, 66 mmol) in concentrated hydrochloric acid (250 mL). The resulting mixture is stirred at 0° C. for 15 min and then at room temperature for 30 min. The temperature is lowered to −5° C. and a solution of tin (II) chloride dihydrate (44.4 g, 197 mmol) in concentrated hydrochloric acid (170 mL) is added drop wise. The resulting suspension is stirred at −5° C. for 30 min and is then allowed to warm up to room temperature over 1 h. The off-white solids are isolated by filtration, washed with cold water and then with diethyl ether and finally dried to afford the desired product (18.04 g, 66 mmol, quantitative yield) (HPLC-MS Method 3: retention time: 2.129 min, m/z 235.1).

Workup

waitat room temperature for 30 min
customis lowered to −5° C.
stirringThe resulting suspension is stirred at −5° C. for 30 min
temperatureto warm up to room temperature over 1 h
customThe off-white solids are isolated by filtration
washwashed with cold water
dry with materialwith diethyl ether and finally dried

Sources & evidence

ORD record: ord-12437ef4392e42c098ee99a302883dd4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096599B2

Reaction notes

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