Methane → HCID 178505406, compound

HRID 1004572Notes

Reaction equation

HRID 1004572 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:6][C:5]([NH2:13])=[C:4]([NH2:14])[CH:3]=1.[C:15](=S)=[S:16].[OH-].[K+].C>C(O)C.O>[F:1][C:2]1[C:7]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:6][C:5]2[N:13]=[C:15]([SH:16])[NH:14][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 10465169HCID 10465169, compound

Product 1

HCID 178505406HCID 178505406, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

The diamine (6.7 g, 0.035 mol) (obtained in step 4 above) was dissolved in ethanol (20 mL) and added to a stirred mixture of carbon disulfide (3.0 g, 0.04 mol), potassium hydroxide (2.3 g, 0.04 mol), water (5 mL) and ethanol (15 mL). The resultant solution was refluxed for 6 h. Animal charcoal (2.0 g) was added and further refluxed for 1 h. The mixture was filtered and washed with hot water. A mixture of acetic acid and water (1:2, 15 mL) was added to the filtrate slowly with vigorous stirring to separate 6-fluoro-5-(imidazol-1-yl)-2-mercapto-1H-benzimidazole (5.0 g, 60%) as a brown solid. mp 280° C. (decomp.); IR (KBr) 3078, 1481 cm-1 ; 1H NMR (DMSO-d6) δ 2.20 (s, 1H, SH), 7.10 (s, 1H), 7.24 (d, J=6.0 Hz, 1H), 7.26 (d, J=4.1 Hz, 1H), 7.56 (s, 1H), 8.00 (s, 1H), 12.90 (brs, 1H, NH); Mass (m/z) 234 (M+.).

Workup

  1. temperaturefurther refluxed for 1 h
  2. filtrationThe mixture was filtered
  3. washwashed with hot water
  4. additionA mixture of acetic acid and water (1:2, 15 mL)
  5. additionwas added to the filtrate slowly
  6. customto separate 6-fluoro-5-(imidazol-1-yl)-2-mercapto-1H-benzimidazole (5.0 g, 60%) as a brown solid

Sources & evidence

ORD record
ord-9cb100df7e064d638039fc754ff51fbe
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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