Phosphorus oxychloride → HCID 178430969, compound

HRID 968798Notes

Reaction equation

HRID 968798 reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[C:5]([C:11](O)=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].O=P(Cl)(Cl)Cl.S(N)([NH2:25])(=O)=O>S1(CCCC1)(=O)=O>[CH3:1][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[C:5]([C:11]#[N:25])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 82267SulfamideHCID 178430971HCID 178430971, compound

Product 1

HCID 178430969HCID 178430969, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-Methyl-6-nitro-1H-benzimidazole-4-carboxylic Acid (23) (16.99 g, 76.90 mmol), POCl3 (15.76 mL, 169 mmol), and sulfamide (14.767 g, 154 mmol) in sulfolane (77 mL) is heated to about 120° C. for about 3 hours. The reaction mixture is cooled to ambient temperature and added to ice water (1 L). The resultant mixture is cooled to about 0° C. filtered to provide 7-Methyl-6-nitro-1H-benzimidazole-4-carbonitrile (24), as an off white solid (12.54 g, 80% Yield).

Workup

  1. temperatureThe reaction mixture is cooled to ambient temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-04deb647738c4d0eaf145939f96f16da
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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