Toluene → HCID 15085579, compound

HRID 1607523Notes

Reaction equation

HRID 1607523 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:11]([N:13]([CH2:16]C)CC)C.C(Cl)(Cl)=[O:19].C1(C)C=CC=CC=1>O1CCCC1>[CH3:11][NH:13][C:16](=[O:19])[NH:10][C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 15085579HCID 15085579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl-3-amino-thiophene-2-carboxylate (5 g, 31,8 mmole) and triethylamine (4,43 ml, 31,8 mmole) in dry tetrahydrofuran (100 ml) was added dropwise a 20% phosgene solution in toluene (31,8 mmole). After the addition had been completed the mixture was heated to reflux for 30 min, followed by filtration at room temperature. The filtrate was evaporated in vacuo, whereafter the crystalline residue was suspended in water (200 ml). Filtration of the suspension left the title compound as white crystals. M.p. 141°-142° C.

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureto reflux for 30 min
  4. filtrationfollowed by filtration at room temperature
  5. customThe filtrate was evaporated in vacuo, whereafter the crystalline residue
  6. filtrationFiltration of the suspension
  7. waitleft the title compound as white crystals

Sources & evidence

ORD record
ord-416f9324956a49c688a00cd94c5dbc9e
Source dataset
uspto-grants-1989_09
Patent number
US04866065

Reaction notes

Loading…