Thiourea → HCID 178527908, compound

HRID 1108779Notes

Reaction equation

HRID 1108779 reaction equation
Cl[C:2]1[C:3]2[NH:10][CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1.NC(N)=[S:13]>C(O)C>[NH:10]1[C:3]2[C:2](=[S:13])[NH:7][CH:6]=[N:5][C:4]=2[P:8]=[CH:9]1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 178478399HCID 178478399, compound2×

Product 1

HCID 178527908HCID 178527908, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 7-chloro-1H-1,3-azaphospholo[4,5-d]pyrimidine (compound 14, 0.23 g, 1.33 mmol), thiourea (0.15 g, 2.0 mmol) and absolute ethanol (10 mL) was heated under reflux for 90 min with stirring under anhydrous conditions. The reaction mixture was cooled to 25° C. and then the solvent was evaporated in vacuo. The residue was sonicated with ice-cold water (10 mL) and the precipitate was collected by filtration, washed with cold water (3×5 mL) and dried over P2O5 in vacuo first at 25° C. and then at 100° C. to yield 0.12 g (55%) of the title compound, mp>300° C. Ir (KBr): ν710 (=P-C), 1170 and 1200 (-P=CH), 1580 (C=S), and 3280 (NH) cm-1. Uv (MeOH): λmax230 nm (ε19,400), 276 (9400), and 338 (17,200). 1H nmr (DMSO-d6): 8.11 (s, 1 H, C5H), 8.93 (dd, 1 H, JC2H,NH =5.4 Hz, JC2H,P =39.6 Hz, C2H), δ 13.15 (s, 1 H, NH), and 13.82 (s, 1 H, NH). Anal. Calcd. for C5H4N3PS.H2O: C, 32.08; H, 3.23; N, 22.45; S, 17.13. Found: C, 32.39; H, 3.61; N, 22.54; S, 17.40. ##STR11##

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 min
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was sonicated with ice-cold water (10 mL)
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with cold water (3×5 mL)
  7. dry with materialdried over P2O5 in vacuo first at 25° C.

Sources & evidence

ORD record
ord-fe6e340439f54ec5a77b238e9094b336
Source dataset
uspto-grants-2000_05
Patent number
US06069132

Reaction notes

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