Carbon Disulfide → HCID 178480613, compound

HRID 1004577Notes

Reaction equation

HRID 1004577 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH2:15])=[C:4]([NH2:16])[CH:3]=1.[C:17](=S)=[S:18].[OH-].[K+].[K+].[Br-]>O.C(O)C>[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][C:5]2[N:15]=[C:17]([SH:18])[NH:16][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 253877Potassium BromideHCID 106567604-Fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine

Product 1

HCID 178480613HCID 178480613, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6-Fluoro-5-(4-methylpiperazin-1-yl)-2-mercapto-1H-benzimidazole (15.0 g, 94%) was prepared by a similar procedure to that described in preparation 1 (step 5) using the diamine (14.0 g, 0.06 mol) (obtained in step 3 above), carbon disulfide (6.1 g, 0.08 mol), potassium hydroxide (4.49 g, 0.08 mol), ethanol (70 mL) and water (10 mL). mp 290° C. (decomp.); IR (KBr) 3088, 1481 cm-1 ; 1H NMR (DMSO-d6) δ 2.24 (s, 3H, CH3), 2.50 (t, J=4.3 Hz, 4H, N(CH2)2), 3.00 (t, J=4.4 Hz, 4H, N(CH2)2), 6.78 (d, J=7.3 Hz, 1H), 7.00 (d, J=11.9 Hz, 1H); Mass (m/z) 266 (M+.).

Workup

  1. customthat described in preparation 1 (step 5)

Sources & evidence

ORD record
ord-7d3803438e01451fa13f218ec26fc475
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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