Benzoyl chloride → N-isopropyl-N-(3,4-methylenedioxyphenyl)-N'-benzoyl thiourea

HRID 1973434Notes

Reaction equation

[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-]=C=S.[Na+].C(Cl)(=O)C1C=CC=CC=1.[CH:25]([NH2:28])([CH3:27])[CH3:26].[CH2:29]1[O:37][C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:30]1>C1C=CC=CC=1>[CH:25]([N:28]([C:34]1[CH:33]=[CH:32][C:31]2[O:30][CH2:29][O:37][C:36]=2[CH:35]=1)[C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[S:11])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 16.3 grams benzoyl isothiocyanate, prepared by refluxing 13.6 grams of dried sodium isothiocyanate with 17 grams of benzoyl chloride in 30 ml. of benzene, is slowly added, at room temperature, 28 grams of N-isopropyl-N-(3,4-methylenedioxyphenyl)-amine (prepared as in Example A) in 150 ml. benzene. The reaction mixture is stirred for 30 minutes at 20°C. and a solid forms which is recrystallized from benzene to yield N-isopropyl-N-(3,4-methylenedioxyphenyl)-N'-benzoyl thiourea melting at 152°-154°C.

Workup

customa solid forms which is recrystallized from benzene

Sources & evidence

ORD record: ord-a07019530c7c47cfb39c5beffc951ad7
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03997564

Reaction notes

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