Water → HCID 14626768, compound

HRID 330470Notes

Reaction equation

HRID 330470 reaction equation
[Cl:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[N:9]2[C:15]=1[C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[NH:12][C:11](=O)[CH2:10]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22].C(=O)(O)[O-].[Na+].O>COCCOCCOC>[Cl:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[N:9]2[C:15]=1[C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[NH:12][C:11](=[S:22])[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 14626766HCID 14626766, compound

Product 1

HCID 14626768HCID 14626768, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 12.5 g 13-chloroindolo[1,2-d][1,4]benzodiazepin-6(7H)-one, 22.6 g phosphorus pentasulfide and 8.6 g sodium bicarbonate in 240 ml diglyme was heated at 110° C. for two hours. The resulting mixture was cooled and poured into 2.5 L water to precipitate a solid. The solid was collected, washed with water and dried (P2O5) to give 11.9 g crude product. Recrystallization of 3.3 g from toluene (300 ml) gave 2.08 g fluffy solid, m.p. 280°-282° C. (dec.).

Workup

  1. temperatureThe resulting mixture was cooled
  2. customto precipitate a solid
  3. customThe solid was collected
  4. washwashed with water
  5. dry with materialdried (P2O5)
  6. customto give 11.9 g crude product
  7. customRecrystallization of 3.3 g from toluene (300 ml)

Sources & evidence

ORD record
ord-4b9308dc7bee48b19344bda22e8ab6e6
Source dataset
uspto-grants-1990_01
Patent number
US04897392

Reaction notes

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