Phthalimide → N-methyl-N'-[3-(4-methyl-2-oxazolyl)thiopropyl]thiourea

HRID 2163897Notes

Reaction equation

C1(=O)NC(=O)C2=CC=CC=C12.NN.[CH3:14][N:15]=[C:16]=[S:17].[CH3:18][C:19]1[N:20]=[C:21]([S:24][CH2:25][CH2:26][CH2:27][NH:28]C(N)=S)[O:22][CH:23]=1>>[CH3:14][NH:15][C:16]([NH:28][CH2:27][CH2:26][CH2:25][S:24][C:21]1[O:22][CH:23]=[C:19]([CH3:18])[N:20]=1)=[S:17]

Participants

Reactant 4

HCID 6809Phthalimide

HCID 9321Hydrazine

HCID 11167Methyl isothiocyanate

HCID 86736270N-[3-(4-methyl-2-oxazolyl)thiopropyl]thiourea

Product 1

HCID 12923388N-methyl-N'-[3-(4-methyl-2-oxazolyl)thiopropyl]thiourea

Procedure

Treatment of the phthalimide compound (3.0 g.) with hydrazine (1.53 g.) followed by reaction of the product directly with methyl isothiocyanate (0.73 g.) using the conditions described in Example 132 afforded N-methyl)-N-[3-(4-methyl-2-oxazolyl)thiopropyl]thiourea (1.0 g.). m.p. 73°-74° (from ethanol-ether-n-hexane).

Sources & evidence

ORD record: ord-62fa46014e2640698d84a9d45967b214
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04137234

Reaction notes

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