Tin tetrachloride → HCID 136377198, compound

HRID 624545Notes

Reaction equation

HRID 624545 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][C:12]([CH3:17])=[CH:13][C:14]=2[C:15]#[N:16])=[C:5]([N+:18]([O-])=O)[CH:4]=1)#[N:2].[Sn](Cl)(Cl)(Cl)[Cl:22]>C(O)C.Cl>[ClH:22].[NH2:16][C:15]1[C:14]2[CH:13]=[C:12]([CH3:17])[S:11][C:10]=2[NH:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:18]=1

Participants

5

Reactant 2

HCID 24287Tin tetrachlorideHCID 86711143HCID 86711143, compound

Product 1

HCID 136377198HCID 136377198, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-(4-Cyano-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile, prepared as described in the previous step, (0.52 g) in ethanol (5 mL), was added tine chloride (1.36 g, 7.2 mmol) in 6 N HCl. The mixture was heated in an 85° C. oil bath for 3 hours and then cooled in ice bath. The solid was filtered, washed with water, and dried to brown give the title compound as a brown solid containing inorganic salt, which was used in the next step without additional purification. LC-MS: m/z 255 (M+1 of free base). 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 11.18 (br, 1H), 10.09 (s, 1H), 9.35 (br, 1H), 8.94 (br, 1H), 7.54 (d, 1H), 7.27 (s, 1H), 6.95 (d, 1H), 2.26 (s, 3H).

Workup

  1. customprepared
  2. temperaturecooled in ice bath
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f43f18ea65ad4b2589c964268e2330f8
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

Loading…