Dichloromethane → HCID 178515982, compound

HRID 539552Notes

Reaction equation

HRID 539552 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]3[N:17]=[N:18][NH:19][CH:20]=3)=[C:9]([OH:21])[C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24].[Al].C(Cl)Cl>CO>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]3[N:17]=[N:18][NH:19][CH:20]=3)=[C:9]([OH:21])[C:8]2=[S:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14817Phosphorus sulfide (P2S5)HCID 5359268AluminumHCID 178516889HCID 178516889, compound

Product 1

HCID 178515982HCID 178515982, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
175 °C

Procedure

159b (0.062 g, 0.21 mmol) was ground together with P4S10 (0.047 g, 0.105 mmol) in mortar and pestle to form grey powder. The powder was stirred under argon in a flask fitted with condenser and heated to 175° C. for 2 h. The reaction flask was covered with aluminum foil during reaction. After 2 h of reaction, flask was cooled down to room temperature. 25 mL of CH2Cl2:MeOH (10%) mixtures was added and stirred for 15 min. This reaction mixture then washed with water (2×30 mL). Organic layer dried with Na2SO4 and evaporated to yield crude product which was purified by prep-TLC (Eluent —CH2Cl2:MeOH (8%) to give 162b (0.04 g, 60%) as olive green solid. 1H NMR (400 MHz, CDCl3) δ 8.47 (s, 1H), 7.82 (m, 3H), 7.50 (d, J=6.5 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 7.34 (t, J=7.4 Hz, 1H), 6.97 (m, 1H), 6.66 (m, 1H), 4.62 (t, J=6.9 Hz, 2H), 4.48 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 168.59, 155.22, 148.03, 131.85, 130.17, 128.84, 128.29, 125.61, 119.84, 113.87, 112.28, 54.99, 46.95, 28.02. HRMS (EI) calcd for C16H16N4OS [M]+ 312.104. found 312.1060.

Workup

  1. customto form grey powder
  2. customfitted with condenser
  3. customAfter 2 h of reaction, flask
  4. temperaturewas cooled down to room temperature
  5. stirringstirred for 15 min
  6. washThis reaction mixture then washed with water (2×30 mL)
  7. dry with materialOrganic layer dried with Na2SO4
  8. customevaporated
  9. customto yield crude product which
  10. customwas purified by prep-TLC (Eluent —CH2Cl2

Sources & evidence

ORD record
ord-78b0b78040b14469984ab86f18d84b03
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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