Hydrochloric Acid → N-[7,7-Di(phenylsulfanyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]-N'-ethylurea

HRID 9158Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15](=O)[CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CCO>[C:17]1([S:23][C:15]2([S:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:10]=3)[C:9]3[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=3[CH2:12][CH2:13][CH2:14]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of N-ethyl-N′-(7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)urea (1.0 g, 4.18 mmol) and thiophenol (0.59 mL, 4.74 mmol) in EtOH (20 mL) was saturated with HCl (g) at about 0° C. The reaction mixture was stirred at about 20° C. for about 2 hrs then a second portion of thiophenol (0.59 mL, 4.74 mmol) was added and the reaction mixture stirred for about another 2 hrs. The ethanol was removed in vacuo and H2O was added. The aqueous phase was neutralized by addition of 2M NaOH and the product was extracted into CH2Cl2 (4 times). The combined organic phases were dried over MgSO4. Evaporation of the solvent gave 1.85 g (quantitative yield) pure product.

Workup

stirringthe reaction mixture stirred for about another 2 hrs
customThe ethanol was removed in vacuo and H2O
additionwas added
additionThe aqueous phase was neutralized by addition of 2M NaOH
extractionthe product was extracted into CH2Cl2 (4 times)
dry with materialThe combined organic phases were dried over MgSO4
customEvaporation of the solvent

Sources & evidence

ORD record: ord-2b6a64fb918f4c86bf8bb7e50346ffdf
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

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