Stannous chloride dihydrate → HCID 68905524, compound

HRID 2110916Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[N:16]([O-])=O.[Na+].O.O.[Sn](Cl)[Cl:23]>Cl.O>[ClH:23].[NH:1]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:13])([F:14])[F:15])[NH2:16]

Participants

Conditions

Temperature: -20 °C

Procedure

6.54 g (30 mmol) methyl 4-amino-3-trifluoromethyl-benzoate are suspended in 50 ml 32% hydrochloric acid and cooled to −20° C. A solution of 2.28 g (33 mmol) sodium nitrite in 20 ml of water is added dropwise. The mixture is stirred for 3 hours at −20° to −10° C., then 27.08 g (120 mmol) tin-(II)-chloride dihydrate in 30 ml hydrochloric acid are added dropwise within 0.25 hours. The reaction mixture is stirred for 2 hours at −10° C., then acidified with cooling. The suspension is suction filtered through kieselguhr and washed with chloroform. The phases of the filtrate are separated, the aqueous phase is extracted with chloroform. The combined organic phases are dried and evaporated to dryness. The residue is precipitated as the hydrochloride, then stirred with diethyl ether.

Workup

stirringThe reaction mixture is stirred for 2 hours at −10° C.
temperaturewith cooling
filtrationfiltered through kieselguhr
washwashed with chloroform
customThe phases of the filtrate are separated
extractionthe aqueous phase is extracted with chloroform
customThe combined organic phases are dried
customevaporated to dryness
customThe residue is precipitated as the hydrochloride
stirringstirred with diethyl ether

Sources & evidence

ORD record: ord-276a2ce8f2c04a97885564d8d7c7e426
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517995B2

Reaction notes

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