Toluene → HCID 13742722, compound

HRID 1607526Notes

Reaction equation

HRID 1607526 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:12]([N:14]([CH2:17]C)CC)C.C(Cl)(Cl)=[O:20].C1(C)C=CC=CC=1.CN>O1CCCC1>[CH3:12][NH:14][C:17](=[O:20])[NH:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 5

HCID 1140TolueneHCID 6329MethylamineHCID 6371PhosgeneHCID 8471TriethylamineHCID 1988156Ethyl 2-aminothiophene-3-carboxylate

Product 1

HCID 13742722HCID 13742722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred soIution of ethyl 2-amino-thiophene-3-carboxylate (5,0 g, 29 mmol) and triethylamine (4,1 ml, 29 mmol) in dry tetrahydrofuran (100 ml) was added a 20% solution of phosgene in toluene (16 ml, 32 mmol). The mixture was heated to reflux for 3 h, then cooled to room temperature and exposed to a gaseous stream of methylamine for 10 min. After additional stirring for 30 min., the mixture was filtered and the filtrate was evaporated in vacuo, whereafter the crystalline residue was suspended in water, filtered off, and dried to give the title compound as colourless crystals, m.p. 127° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated in vacuo, whereafter the crystalline residue
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-b8413b2e4b244039b5c6f7c7a354f838
Source dataset
uspto-grants-1989_09
Patent number
US04866065

Reaction notes

Loading…