Water → HCID 12906311, compound

HRID 2059002Notes

Reaction equation

HRID 2059002 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-a8ecacd348dd402babf75570d1865db6
Source dataset
uspto-grants-1982_03
Patent number
US04321200

Reaction notes

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