Ammonia → 1360899-50-8

HRID 1051172Notes

Reaction equation

HRID 1051172 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[C:6]([NH2:8])[CH:7]=1.[CH:11](O)=O.O.N>Cl>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]2[N:9]=[CH:11][NH:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 284Formic AcidHCID 962WaterHCID 534141905-Bromobenzene-1,2,3-triamine

Product 1

HCID 683865391360899-50-8Yield 96.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred suspension of 5-bromobenzene-1,2,3-triamine (81.5 g, 403 mmol) in HCl conc (2400 mL) at rt was added formic acid (46 mL, 1210 mmol, 3 eq). After stirring at reflux for 90 min, water (500 mL) was added to the suspension, and the pH was adjusted to 8 using ammonia (33% aqueous solution). After extraction with ethyl acetate (3×1000 mL), the organic phase was washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated in vaccuo. The crude product was trituarated with diethyl ether (200 mL), filtered and dried to yield 82.3 g 6-bromo-1H-benzimidazol-4-amine (96.3%).

Workup

  1. temperatureat reflux for 90 min
  2. extractionAfter extraction with ethyl acetate (3×1000 mL)
  3. washthe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vaccuo
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3ea124869c254c52921d0c6a2353794c
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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