Toluene → HCID 18322361, compound

HRID 1698892Notes

Reaction equation

HRID 1698892 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>O>[C:16]([NH:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:8])[CH3:9])[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 2777503Methyl 3-amino-5-tert-butylthiophene-2-carboxylate

Product 1

HCID 18322361HCID 18322361, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3-amino-5-tert-butylthiophene-2-carboxylate (20.0 g, 93.9 mmol), benzyl chloroformate (80.4 mL, 563 mmol), Na2CO3 (1.10 g, 9.93 mmol), toluene (400 mL) and water (50 mL) was heated at the reflux temp. for 18 h. Volatiles were removed under reduced pressure. The resulting oil was dissolved in EtOAc, washed with water and a concentrated NaCl solution, dried (MgSO4) and concentrated under reduced pressure to afford methyl 3-(N-carbobenzyloxyamino)-5-tert-butylthiophene-2-carboxylate as a crude oil in quantitative yield.

Workup

  1. customVolatiles were removed under reduced pressure
  2. dissolutionThe resulting oil was dissolved in EtOAc
  3. washwashed with water
  4. dry with materiala concentrated NaCl solution, dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a1b03a5a2a94e1bb7a556b792f47628
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

Loading…