Phenol → HCID 24785529, compound

HRID 2239324Notes

Reaction equation

HRID 2239324 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:8][C:9]=1[N:10]=[CH:11][N:12]([CH3:14])C)=[O:4].NC[CH2:24][C:25]1[CH:37]=[CH:36][C:28]([C:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1.C1(O)C=CC=CC=1>>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:7]2[S:6][C:5]3[C:3](=[O:4])[N:12]([CH2:14][CH2:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 404302424-(2-Aminoethyl)-N,N-diethylbenzamide

Product 1

HCID 24785529HCID 24785529, compound

Procedure

5-(4-Chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.100 g, 0.310 mmol), 4-(2-amino-ethyl)-N,N-diethyl-benzamide (0.082 g, 0.372 mmol) and phenol (1.0 g) were stirred at 135° C. for 2 hours. The reaction mixture was allowed to cool to r.t. and the product precipitated by the addition of MeOH (16 mL). The precipitate was filtered off and washed with MeOH to give the title compound. Yield: 0.058 g (40%). 1H NMR (400 MHz, CDCl3) δ 7.69 (s, 1H), 7.61 (d, 2H, J=8.67 Hz), 7.39-7.44 (m, 3H), 7.30 (d, 2H, J=8.19 Hz), 7.18 (d, 2H, J=8.19 Hz), 4.23 (t, 2H, J=7.05 Hz), 3.51 (bs, 1H), 3.46 (d, 2H, J=5.39 Hz), 3.21 (bs, 1H), 3.12 (t, 2H, J=6.64 Hz), 1.21 (bs, 3H), 1.08 (bs, 3H).

Workup

  1. customthe product precipitated by the addition of MeOH (16 mL)
  2. filtrationThe precipitate was filtered off
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-a0af246f208d4edf97547b48f3b17015
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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