Sodium Carbonate → HCID 10262941, compound

HRID 743158Notes

Reaction equation

HRID 743158 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C([O-])([O-])=O.[Na+].[Na+].[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][N:29]=2)[CH2:24][C:23]1=O.[C:32]([O:35][C:36]1[CH:44]=[C:43]2[C:39]([CH2:40][C:41](=O)[N:42]2[CH3:45])=[CH:38][CH:37]=1)(=[O:34])[CH3:33]>C1COCC1>[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][N:29]=2)[CH2:24][C:23]1=[S:2].[C:32]([O:35][C:36]1[CH:44]=[C:43]2[C:39]([CH2:40][C:41](=[S:2])[N:42]2[CH3:45])=[CH:38][CH:37]=1)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 10398026HCID 10398026, compoundHCID 10997193HCID 10997193, compound

Product 2

HCID 10262941HCID 10262941, compoundHCID 103296361,3-Dihydro-1-methyl-2H-pyrrolo[2,3-b]pyridine-2-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

P2S5 (3.80 g, 8.10 mmol) was added to a vigorously stirred suspension of Na2CO3 (0.88 g, 8.10 mmol) in THF (30 mL). After the mixture had become homogeneous (ca. 15 minutes), a solution of 1-methyl-7-aza-2-indolinone [VII: R1 =7-aza, R3 =Me] (1.00 g) in THF (10 mL) was added and stirring was continued for 18 hours at 20° C. Solvent was removed under reduced pressure, and the residue was partitioned between EtOAc and water. Workup of the organic layer, and chromatography of the residue on silica gel (elution with EtOAc/petroleum ether (1:5)) gave 1-methyl-7-aza-2-indolinethione [IX: R1 =7-aza, R3 =Me] (0.81 g, 73%); mp (EtOAc/petroleum ether) 130°-133° C.

Workup

  1. custom(ca. 15 minutes)
  2. customSolvent was removed under reduced pressure
  3. customthe residue was partitioned between EtOAc and water

Sources & evidence

ORD record
ord-d085b3684c424b429ac4cae4bc980cf3
Source dataset
uspto-grants-1996_09
Patent number
US05556874

Reaction notes

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