4-Methylmorpholine → HCID 69543487, compound

HRID 1837612Notes

Reaction equation

HRID 1837612 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([OH:12])=O)=[CH:8][CH:9]=1)=[O:4].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:28][CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:12])[NH:28][CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 83551-NaphthalenemethanamineHCID 62365Isobutyl chloroformateHCID 8183525-(Methoxycarbonyl)thiophene-2-carboxylic acid

Product 1

HCID 69543487HCID 69543487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.9 g Thiophene-2,5-dicarboxylic acid monomethyl ester and 1.2 mL N-methylmorpholine is dissolved in 20 mL of CH2Cl2 at −10° C. To this solution is added 1.5 mL isobutyl chloroformate. After 10 min of stirring, 1.7 mL 1-(aminomethyl)-naphthalene in 5 mL of CH2Cl2 is added. The cooling bath is removed and the reaction mixture is allowed to reach rt. After 90 min, 10 mL of water and 10 mL 2N HCl are added. The phases are separated, and the organic phase is washed with water. After evaporation of the solvent there is obtained 4.4 g crude 5-[(naphtalen-1-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid methyl ester (1b) which is purified by recrystalisation from ethylacetate, petrol ether, yielding 58%, mp 125° C.

Workup

  1. customThe cooling bath is removed
  2. customto reach rt
  3. waitAfter 90 min
  4. addition10 mL of water and 10 mL 2N HCl are added
  5. customThe phases are separated
  6. washthe organic phase is washed with water
  7. customAfter evaporation of the solvent there

Sources & evidence

ORD record
ord-c82c9b6d535a49978fb8a883d293fcef
Source dataset
uspto-grants-2004_08
Patent number
US06784173B2

Reaction notes

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