Hydrochloric Acid → 3-Benzoyl-1-methyl-2-indolinethione

HRID 743159Notes

Reaction equation

HRID 743159 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[S:11].[H-].[Na+].C(N=[N+]=[N-])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].Cl>C1COCC1>[C:15]([CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]1=[S:11])(=[O:16])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 261561,3-Dihydro-1-methyl-2H-indole-2-thioneHCID 109865532-Azido-1-phenylethanone

Product 1

HCID 104231073-Benzoyl-1-methyl-2-indolinethione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 1-methyl-2-indolinethione (0.50 g, 3.06 mmol) in dry THF (3 mL) was added dropwise at 20° C. under N2 to a stirred suspension of NaH (0.13 g of a 60% w/w suspension in mineral oil, 3.37 mmol) in THF (2 mL). After gas evolution had ceased (5 minutes), a solution of the above phenacyl azide in THF (2 mL) was added dropwise, and the mixture was stirred at 20° C. for 1 hour, then poured into 6N HCl and extracted with EtOAc. The residue from the organic layer was chromatographed on silica gel. Elution with CH2Cl2 /petroleum ether (3:7) gave foreruns, and elution with CH2Cl2 /petroleum ether (2:3) gave 3-benzoyl-1-methyl-2-indolinethione [XV: R1 =H, R3 =Me, R5 =C6H5] (24) (0.31 g, 38%); mp (trituration from MeOH) 132°-134° C.

Workup

  1. custom(5 minutes)
  2. extractionextracted with EtOAc
  3. customThe residue from the organic layer was chromatographed on silica gel
  4. washElution with CH2Cl2 /petroleum ether (3:7)
  5. customgave
  6. washforeruns, and elution with CH2Cl2 /petroleum ether (2:3)

Sources & evidence

ORD record
ord-0b487add763e46dea44b1761704f4337
Source dataset
uspto-grants-1996_09
Patent number
US05556874

Reaction notes

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