Ethanol → HCID 178516368, compound

HRID 1004582Notes

Reaction equation

HRID 1004582 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH2:15])=[C:4]([NH2:16])[CH:3]=1.[C:17](=S)=[S:18].C(O)C.[K+].[Br-]>O>[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([OH: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

6

Reactant 4

HCID 702EthanolHCID 6348Carbon DisulfideHCID 253877Potassium BromideHCID 18792794HCID 18792794, compound

Product 1

HCID 178516368HCID 178516368, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Fluoro-5-(4-hydroxypiperidin-1-yl)-2-mercapto-1H-benzimidazole (4.5 g, 62%) was prepared by a similar procedure to that described in preparation 1 (step 5) using the diamine (6.0 g, 0.027 mol) (obtained in step 2 above), carbon disulfide (3.9 g, 0.052 mol), ethanol (30 mL) and water (5 mL). mp 268-269° C.; IR (KBr) 3397, 3124, 1487 cm-1 ; 1H NMR (DMSO-d6) δd 1.45-1.56 (m, 2H, CH2), 1.60-1.87 (m, 2H, CH2), 2.24 (s, 1H, SH), 2.64-3.92 (m, 2H, NCH2), 3.11-3.17 (m, 2H, NCH2), 3.30-3.60 (m, 1H, CH), 4.30 (brs, 1H, OH), 6.70 (d, J=7.4 Hz, 1H), 7.00 (d, J=12.6 Hz, 1H), 12.00 (brs, 1H, NH); Mass (m/z) 267 (M+.).

Workup

  1. customthat described in preparation 1 (step 5)

Sources & evidence

ORD record
ord-36cc18969e034cab977d2d9312dddde2
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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