Thiourea → 2-(Quinol-3-ylmethyl)-isothiourea dihydrochloride

HRID 1701914Notes

Reaction equation

[ClH:1].[Cl:2][CH2:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.[NH2:14][C:15]([NH2:17])=[S:16]>C(O)C>[ClH:2].[ClH:1].[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([CH2:3][S:16][C:15](=[NH:14])[NH2:17])[CH:5]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 3-chloromethylquinoline hydrochloride (46.4 g) in ethanol (160 cc), at 70° C., is added dropwise, in the course of 10 minutes, to a suspension of thiourea (19.7 g) in boiling ethanol (110 cc). The reaction mixture is stirred for 1 hour 30 minutes at the boil and then cooled to 10° C. The resulting crystals are filtered off, washed twice with ethanol (100 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. 2-(Quinol-3-ylmethyl)-isothiourea dihydrochloride (59.3 g), melting at 226°-228° C., is thus obtained.

Workup

filtrationThe resulting crystals are filtered off
washwashed twice with ethanol (100 cc in total)
customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C

Sources & evidence

ORD record: ord-bc71b5380a834860be2fb2fadbe6ad29
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04379154

Reaction notes

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