Toluene → HCID 10681174, compound

HRID 842614Notes

Reaction equation

HRID 842614 reaction equation
[NH2:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C.[C:22](Cl)(Cl)=[O:23].C1(C)C=CC=CC=1>C1COCC1>[N:1]([C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12])=[C:22]=[O:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 13793447Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 10681174HCID 10681174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate (0.624 g, 3.00 mmol), prepared as described in (Journal of Heterocyclic Chemistry, 24: 85 (1987), and triethylamine (0.84 mL, 6.0 mmol) in THF (20 mL) at −78° C. was treated with a 1.93M solution of phosgene in toluene (1.7 mL, 3.3 mmol), stirred for 2 hours at −78° C., concentrated, and used in subsequent steps without further purification.

Workup

  1. customat −78° C.
  2. concentrationconcentrated
  3. customused in subsequent steps without further purification

Sources & evidence

ORD record
ord-870b7a1eb78446e280b03da6a91d2c7e
Source dataset
uspto-grants-2002_04
Patent number
US06376488B1

Reaction notes

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