Boron tribromide → 1,2-Benzenediol, 5-(2-amino-4-thiazolyl)-3-nitro-, monohydrobromide

HRID 274466Notes

Reaction equation

HRID 274466 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([OH:16])=[C:9]([O:17]C)[CH:8]=2)[N:6]=1.B(Br)(Br)[Br:20]>C(Cl)Cl>[BrH:20].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([OH:17])[C:10]([OH:16])=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=2)[N:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 214592034-(2-Amino-4-thiazolyl)-2-methoxy-6-nitrophenol

Product 1

HCID 57479831,2-Benzenediol, 5-(2-amino-4-thiazolyl)-3-nitro-, monohydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 267.3 mg of 4-(2-amino-4-thiazolyl)-2-methoxy-6-nitrophenol in 10 ml of dry methylene chloride is treated at -20° with 1.25 g of boron tribromide. After the addition the mixture is stirred at -20° for a further 1 hour and at room temperature without cooling for 18 hours. The reaction mixture is then evaporated, the residue is treated cautiously with water and stirred at 50° for 30 minutes. After cooling to room temperature the mixture is suction filtered and the crude product is removed by filtration and washed with a small amount of water. There is obtained 5-(2-amino-4-thiazolyl)-3-nitropyrocatechol hydrobromide of m.p. 244°-246° (from methanol).

Workup

  1. additionAfter the addition the mixture
  2. temperaturewithout cooling for 18 hours
  3. customThe reaction mixture is then evaporated
  4. additionthe residue is treated cautiously with water
  5. stirringstirred at 50° for 30 minutes
  6. temperatureAfter cooling to room temperature the mixture
  7. filtrationfiltered
  8. customthe crude product is removed by filtration
  9. washwashed with a small amount of water

Sources & evidence

ORD record
ord-ce1fa227ee234d6a8a40edcace2564d6
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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