Benzoyl isothiocyanate → tert-butyl N-(4-{[(benzoylamino)carbothioyl]amino}benzyl)carbamate

HRID 1976119Notes

Reaction equation

HRID 1976119 reaction equation
NCC1C=CC(NC2SC3CCCC4C=CC(F)=CC=4C=3N=2)=CC=1.[NH2:25][C:26]1[CH:40]=[CH:39][C:29]([CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:28][CH:27]=1.[C:41]([N:49]=[C:50]=[S:51])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1COCC1>[C:41]([NH:49][C:50]([NH:25][C:26]1[CH:40]=[CH:39][C:29]([CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[CH:28][CH:27]=1)=[S:51])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 87828853N2-[4-(aminomethyl)phenyl]-9-fluoro-5,6-dihydro-4H-benzo-[6,7]cyclohepta[d][1,3]thiazol-2-amine tert-butyl N-(4-aminobenzyl)carbamate

Product 1

HCID 22000388tert-butyl N-(4-{[(benzoylamino)carbothioyl]amino}benzyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N2-[4-(aminomethyl)phenyl]-9-fluoro-5,6-dihydro-4H-benzo[6,7]cyclohepta[d][1,3]thiazol-2-amine-tert-butyl N-(4-aminobenzyl)carbamate (6.00 g, 27.0 mmol) in anhydrous THF (50 ml) was added benzoylisothiocyanate (4.43 g, 27.0 mmol). The solution was stirred for 2 hours and the solvent removed in vacuo to yield 100% (10.4 g) of the protected thiourea as a yellow solid: m.p. 161-163° C. 1H-NMR (CDCl3) δ 1.45 (9H, s), 4.33 (2H, d), 4.85 (1H, broad), 7.34 (2H, d), 7.60 (5H, m), 7.90 (2H, d), 9.13 (1H, s), 12.58 (1H, s); 386 (ESMS, MH+).

Workup

  1. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a16f939a7d6b4c44b5f1919274ab650d
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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