849333-58-0 → HCID 67246733, compound

HRID 1173341Notes

Reaction equation

HRID 1173341 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:12](Cl)(=O)=O>Cl.O.C(O)(=O)C>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[SH:12]

Participants

5

Reactant 1

HCID 45357699849333-58-0

Product 1

HCID 67246733HCID 67246733, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of stannous chloride (196 g, 0.86 mol) in concentrated hydrochloric acid (250 mL) and water (55 mL) was added to a stirred suspension of compound of Example 1c (68 g, 0.217 mol) in acetic acid (580 mL) at 80° C., over a period of 20 min. The reaction mixture was stirred at 80° C. for 4 h. The reaction mixture was cooled, poured into water (500 mL) with stirring and digested at 80° C. for 30 min. The solid was filtered, washed with water till filtrate was neutral and dried to obtain the title compound. Yield: 48 g (90%); 1H NMR (DMSO-d6, 300 MHz): δ 2.40 (s, 3H, CH3), 7.70 (s, 1H, Ar), 7.84 (s, 1H, Ar); MS: m/e (ES−) 491 (M−1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringwith stirring
  3. waitdigested at 80° C. for 30 min
  4. filtrationThe solid was filtered
  5. washwashed with water till filtrate
  6. customdried

Sources & evidence

ORD record
ord-355b2ee4357c4b8cbcc4215b1f6c5d2d
Source dataset
uspto-grants-2010_11
Patent number
US07834052B2

Reaction notes

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