Ethylenethiourea → HCID 10291641, compound

HRID 2183615Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10](=O)[CH2:11][CH3:12])=[CH:7][CH:8]=[CH:9][C:2]1=2.[Br-:14].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[NH:47]1[CH2:51][CH2:50][NH:49][C:48]1=[S:52]>>[BrH:14].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10]3[N:49]4[CH2:50][CH2:51][N:47]=[C:48]4[S:52][C:11]=3[CH3:12])=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

Reactant 3

HCID 2723650Ethylenethiourea

HCID 17977687Phenyltrimethylammonium bromide dibromide

HCID 224739661-(Benzo[b]thiophen-4-yl)propan-1-one

Product 1

HCID 10291641HCID 10291641, compound

Procedure

1-(Benzo[b]thiophen-4-yl)propan-1-one (32.3 g; prepared in a manner similar to that described above) was reacted with phenyltrimethylammonium tribromide (63.9 g) followed by 2-imidazolidinethione (17.4 g) using methodology similar to that described in Example 9 Method A to give 3-(benzo[b]thiophen-4-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (46.8 g) as a colourless solid, m.p. 262-264° C. This was combined with a sample of 3-(benzo[b]thiophen-4-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (25.4 g) prepared according to the methodology described in Example 9 Method A. The combined sample was then basified and converted into the hydrochloride salt in a manner similar to that described in Example 9 Method A to give 3-(benzo[b]thiophen-4-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride (46.8 g) as a colourless solid, m.p. 242-245° C.

Workup

customprepared in a manner similar to

Sources & evidence

ORD record: ord-0623de8150ac46248f2c99c45c171b90
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900216B2

Reaction notes

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