Ethanol → HCID 178527806, compound

HRID 1004587Notes

Reaction equation

HRID 1004587 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([NH2:14])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:15](=S)=[S:16].C(O)C.[K+].[Br-]>O>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]3[NH:13][C:15]([SH:16])=[N:14][C:9]=3[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 6348Carbon DisulfideHCID 253877Potassium BromideHCID 133540674-(Piperazin-1-yl)benzene-1,2-diamine

Product 1

HCID 178527806HCID 178527806, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(Piperazin-1-yl)-2-mercapto-1H-benzimidazole (7.9 g, 85%) was prepared by an analogous procedure to that described in preparation 1 (step 5) using the diamine (8.0 g, 0.04 mol) (obtained in step 2 above), carbon disulfide (3.6 g, 0.048 mol), ethanol (40 nmL) and water (4 nmL). mp 260-261° C.; IR (KBr) 3350, 1498 cm-1 ; 1H NMR (DMSO-d6) δ 2.40 (s, 1H, SH), 3.00 (t, J=4.4 Hz, 4H, N(CH2)2), 3.50 (brs, 1H, NH), 4.42 (t, J=4.5 Hz, 4H, N(CH2)2), 6.68 (s, 1H), 6.85 (d, J=8.0 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H) ; Mass (m/z) 234 (M+.).

Workup

  1. customthat described in preparation 1 (step 5)

Sources & evidence

ORD record
ord-a78a1eca757b4423b2ec5a5f115beab6
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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