Water → N-(phenylthioureido)-dihydroisoindole

HRID 1680109Notes

Reaction equation

HRID 1680109 reaction equation
Cl.[NH2:2][N:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C(N(CC)CC)C.[C:19]1([N:25]=[C:26]=[S:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[C:19]1([NH:25][C:26](=[S:27])[NH:2][N:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 233429362,3-dihydro-1H-isoindol-2-amine hydrochloride

Product 1

HCID 12906312N-(phenylthioureido)-dihydroisoindoleYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.7 g (0.01 mole) of N-amino dihydroisoindole hydrochloride in 10 ml of dimethyl formamide was added 1 ml of triethylamine followed by 1.35 g (0.01 mole) of phenylisothiocyanate. The reaction mixture was allowed to stir at room temperature overnight. Water (25 ml) was added, the mixture stirred for 1 hr., and filtered. After drying there was obtained 2.6 g of the desired product, mp: 192°-193° dec. The IR and NMR were consistent with the proposed structure.

Workup

  1. stirringthe mixture stirred for 1 hr
  2. filtration, and filtered
  3. customAfter drying there

Sources & evidence

ORD record
ord-7cf5f4d6146c48a8b9820853ff7a132e
Source dataset
uspto-grants-1981_06
Patent number
US04272284

Reaction notes

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