Trityl chloride → N-(2-methyl-1-(tritylamino)propan-2-ylcarbamothioyl)benzamide

HRID 708165Notes

Reaction equation

HRID 708165 reaction equation
[CH3:1][C:2]([NH2:25])([CH3:24])[CH2:3][NH:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(N)(C)CN.C(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:52]([N:60]=[C:61]=[S:62])(=[O:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>>[CH3:24][C:2]([NH:25][C:61]([NH:60][C:52](=[O:59])[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[S:62])([CH3:1])[CH2:3][NH:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 6456Trityl chlorideHCID 131282-MethylpropylenediamineHCID 68284Benzoyl isothiocyanateHCID 10088037HCID 10088037, compound

Product 1

HCID 86652326N-(2-methyl-1-(tritylamino)propan-2-ylcarbamothioyl)benzamideYield 44%

Procedure

2-Methyl-N1-tritylpropane-1,2-diamine, prepared from 2-methylpropane-1,2-diamine and trityl chloride (EP1204654) in yield of 44%, was coupled with benzoylisothiocyanate to give N-(2-methyl-1-(tritylamino)propan-2-ylcarbamothioyl)benzamide (US2008/45579) which was then reacted with lithium hydroxide to give 1-(2-methyl-1-(tritylamino)propan-2-yl)thiourea. Yield 79%. 1H NMR (400 MHz, CDCl3) δ 7.40-7.12 (m, 16H), 6.30 (s, 1H), 2.38 (d, J=8.3, 2H), 2.15 (t, J=8.3, 1H), 1.31 (s, 6H)

Sources & evidence

ORD record
ord-cb9db3e743cf43a797f1ce06a97b1ae3
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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