4-Methyloxybenzyl chloride → HCID 59702062, compound

HRID 902516Notes

Reaction equation

HRID 902516 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[CH3:11][O:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][C:19]=1[NH2:20])=[O:14]>C(Cl)Cl>[CH3:11][O:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][C:19]=1[NH:20][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:14]

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 59702062HCID 59702062, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

4-Methoxybenzyl chloride (22.8 mL, 167.42 mmol) was added to a solution of methyl-3-amino-thiophene-2-carboxylate (17.55 g, 111 mmol) in dry CH2Cl2 (20 mL). The solution was mixed well. Excess CH2Cl2 was evaporated and the mixture was heated overnight at 85° C. under vacuum (3 torr). The mixture was cooled to room temperature. Hexane was added to the mixture, which was refluxed for 30 min, and cooled to 0° C. The solids formed were filtered, washed by hexane, and dried to yield 28.19 g (91%) of 3-(4-methoxybenzylamino)-thiophene-2-carboxylic acid methyl ester as red solids. 1H NMR (400 MHz, DMSO-d6) δ 3.71 (s, 6H), 4.42 (s, 2H), 6.77 (d, J=5.6 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H), 7.25 (d, J=8.8 Hz, 2H), 7.63 (d, J=5.6 Hz, 1H), ppm; MS m/z=278 amu (M++1).

Workup

  1. additionThe solution was mixed well
  2. customExcess CH2Cl2 was evaporated
  3. temperatureThe mixture was cooled to room temperature
  4. additionHexane was added to the mixture, which
  5. temperaturewas refluxed for 30 min
  6. temperaturecooled to 0° C
  7. customThe solids formed
  8. filtrationwere filtered
  9. washwashed by hexane
  10. customdried

Sources & evidence

ORD record
ord-3a01f171c76a45cfb0191f15da9307e1
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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