Phosphorus oxide (P4O10) → 4,6-Diaminoresorcinol

HRID 1762965

Reaction equation

HRID 1762965 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([OH:11])=[CH:6][C:5]=1[OH:12].S1C2C=CC=CC=2N=C1C1C(C(O)=O)=CC=C(C(O)=O)C=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[NH2:3][C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([OH:11])=[CH:6][C:5]=1[OH:12]

Participants

4

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 27336484,6-Diaminoresorcinol DihydrochlorideHCID 43022361,4-Benzenedicarboxylic acid, 2-(2-benzothiazolyl)-

Product 1

HCID 4588214,6-Diaminoresorcinol

Conditions

Temperature
90 °C

Procedure

4,6-Diamino-1,3-benzenediol dihydrochloride (2.1279 g, 10.0 mmol), 2-benzothiazole terephthalic acid (2.9891 g, 10.0 mmol) and 9.96 g of polyphosphoric acid (77% P2O5) were placed in a resin flask equipped with a mechanical stirrer, nitrogen inlet/outlet tubes, a vacuum connector and a side opening on the resin flask. The solution was heated at 90° C. in vacuo for 20 hours for dehydrochlorination. The reaction mixture was cooled to 50° C., then 6.04 g of P2O5 was added, in vacuo, thereby raising the polymer concentration to 18%. After adding the P2O5, heating was resumed. The mixture was heated at 174° C. for 16 hours, then at 190° C. for 24 hours. Work-up, as in the preceeding Example, gave 3.2 g of polymer with [N]=4.1 dl/g, methanesulfonic acid at 30° C.

Workup

  1. customequipped with a mechanical stirrer, nitrogen inlet/outlet tubes
  2. temperatureThe reaction mixture was cooled to 50° C.
  3. temperatureraising
  4. concentrationthe polymer concentration to 18%
  5. additionAfter adding the P2O5
  6. temperatureheating
  7. temperatureThe mixture was heated at 174° C. for 16 hours
  8. customat 30° C.

Sources & evidence

ORD record
ord-ad1c43b0ed3742e58fcf6daefe6ed866
Source dataset
uspto-grants-1989_05
Patent number
US04835246

Linked notes

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