Water → HCID 12906311, compound

HRID 1680112Notes

Reaction equation

HRID 1680112 reaction equation
Cl.[CH3:2][NH:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.C(N(CC)CC)C.[C:20]1([N:26]=[C:27]=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O.CCOCC>[CH3:2][N:3]([N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)[C:27]([NH:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[S:28]

Participants

7

Reactant 4

HCID 962WaterHCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 12906310HCID 12906310, compound

Product 1

HCID 12906311HCID 12906311, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.12 g (0.006 mole) of N-methylamino dihydroisoindole hydrochloride in 10 ml of dimethylformamide was added 1 ml of triethylamine followed by 0.82 g (0.006 mole) of phenylisothiocyanate. The reaction mixture was allowed to stir at room temperature overnight. Water (25 ml) was added and the resulting gummy solid was extracted with ethyl acetate. After drying and filtering, evaporation gave a thick oil which solidified upon adding a small amount of ether and scratching. There was obtained 1.4 g of the desired product, mp: 121°-125° dec. The IR and NMR were consistent with the proposed structure.

Workup

  1. extractionthe resulting gummy solid was extracted with ethyl acetate
  2. customAfter drying
  3. filtrationfiltering
  4. customevaporation
  5. customgave a thick oil which

Sources & evidence

ORD record
ord-7490f2a6889e4445a6e8aa6c56e80435
Source dataset
uspto-grants-1981_06
Patent number
US04272284

Reaction notes

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