Phosphorus sulfide (P2S5) → HCID 21883016, compound

HRID 722106Notes

Reaction equation

HRID 722106 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=[S:14]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 228606HCID 228606, compound

Product 1

HCID 21883016HCID 21883016, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of (2,3-dichloro-phenyl)-acetamide (4.50 g, 22 mmol,) in toluene (50 ml) was treated at r.t. with P2S5 (9.80 g, 22 mmol). The reaction mixture was heated to 90° C. for 1.5 h, cooled to r.t., and filtered. The solid was washed with ether and the washings were combined with the filtrate. The combined solutions were extracted twice with 10% aq. NaOH. The combined aqueous extracts were acidified at 0° C. with HCl. The precipitate was collected and recrystallized from ethyl acetate/hexane to afford (2,3-dichloro-phenyl)-thioacetamide (3.40 g, 16 mmol). HPLC Rt: 5.91 min. 1H-NMR (CDCl3): δ 8.80 (br. s, 1H, NH), 8.5 (d, 1H), 7.42 (d, 1H), 7.30 (t, 1H), 2.82 (s, 3H).

Workup

  1. temperaturecooled to r.t.
  2. filtrationfiltered
  3. washThe solid was washed with ether
  4. extractionThe combined solutions were extracted twice with 10% aq. NaOH
  5. customwere acidified at 0° C. with HCl
  6. customThe precipitate was collected
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-32d594f03b334d6383454566debf5c85
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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