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Dimethylamine → Methyl 4-(dimethylcarbamoyl)benzoate

HRID 1808885
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HRID 1808885 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)=[O:4].[CH3:14][N:15](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:16].F[P-](F)(F)(F)(F)F.CNC.C(N(CC)CC)C>C1COCC1>[CH3:14][N:15]([CH3:16])[C:9]([C:8]1[CH:12]=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)=[O:10]
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참가 물질

6

반응물 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 15513Monomethyl terephthalateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 11106558Methyl 4-(dimethylcarbamoyl)benzoate수율 83%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a soln. of 4-(methoxycarbonyl)benzoic acid (100 mg, 0.555 mmol) in THF (5 ml) was added HATU (211 mg, 0.555 mmol), dimethylamine (0.278 ml, 0.555 mmol) and triethylamine (0.077 ml, 0.555 mmol) at r.t. The mixture was stirred at r.t for 4 hrs. Evaporated to remove the solvent. The residue was dissolved in EtOAc (10 ml), washed w/water (3×), brine. Dried (Na2SO4), and evaporated to afford methyl 4-(dimethylcarbamoyl)benzoate (100 mg, 0.458 mmol, 83% yield) as solid. 1H-NMR (CD3OD, 500 MHz): δ 8.10 (1H, d, J=6.4 Hz), 7.55 (1H, d, J=6.4 Hz), 3.94 (3H, s), 3.13 (3H, s), 2.99 (3H, s). m/e (M+H): 208.1

후처리

  1. customEvaporated
  2. customto remove the solvent
  3. dissolutionThe residue was dissolved in EtOAc (10 ml)
  4. washwashed w/water (3×), brine
  5. dry with materialDried (Na2SO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-67be1f4bfb1c4990b9c4ab6b518c4ab2
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362004B2

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