Phosphorus sulfide (P2S5) → HCID 20605701, compound

HRID 481095Notes

Reaction equation

HRID 481095 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:11]2[C:12](=O)[NH:13][CH2:14][CH2:15][CH2:16][C:10]=2[NH:9][CH:8]=1)=[O:6])[CH2:2][CH3:3].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>N1C=CC=CC=1>[CH2:1]([O:4][C:5]([C:7]1[C:11]2[C:12](=[S:19])[NH:13][CH2:14][CH2:15][CH2:16][C:10]=2[NH:9][CH:8]=1)=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 20605700HCID 20605700, compound

Product 1

HCID 20605701HCID 20605701, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound (500 mg) from Step 1 and P4S10 (2.0 g) in 20 mL of pyridine is heated at 80° C. with stirring overnight. It is cooled and evaporated under vacuum, then diluted with water and stirred. The insoluble material is filtered and the mother liquid is extracted with CH2Cl2/EtOAc (1:4). The combined extract is washed with brine, dried and concentrated to give 120 mg of 4-thioxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-3-carboxylic acid propyl ester.

Workup

  1. temperatureIt is cooled
  2. customevaporated under vacuum
  3. additiondiluted with water
  4. stirringstirred
  5. filtrationThe insoluble material is filtered
  6. extractionthe mother liquid is extracted with CH2Cl2/EtOAc (1:4)
  7. extractionThe combined extract
  8. washis washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e31fd5a0919c49a99bbe2992515296c6
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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