Phenol → HCID 58980792, compound

HRID 1181378Notes

Reaction equation

HRID 1181378 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[CH2:4][CH2:5][S:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:27][C:26]([C:28](OC)=[O:29])=[C:25]([N:32]=[CH:33]N(C)C)[CH:24]=2)=[CH:19][CH:18]=1.C1(O)C=CC=CC=1>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[S:27][C:26]3[C:28](=[O:29])[N:11]([C:10]4[CH:9]=[CH:8][C:7]([S:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:14][CH3:15])=[CH:13][CH:12]=4)[CH:33]=[N:32][C:25]=3[CH:24]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 198633934-[[2-(Diethylamino)ethyl]thio]benzenamine

Product 1

HCID 58980792HCID 58980792, compound

Conditions

Temperature
190 °C

Procedure

The mixture of 4-{[2-(diethylamino)ethyl]sulfanyl}aniline (1.0 mmol, 271 mg), amidine (methyl 5-(4-chlorophenyl)-3-{[(dimethylamino)methylidene]amino]2-thiophenecarboxylate, 1.0 mmol, 322 mg, the preparation of which may be found in the Example J13) and phenol (350 mg) was heated to 190° C. for 20 minutes. The mixture was cooled to room temperature and then washed with methanol. The crude solid product was collected by filtration and then was dissolved in minimum amount of dichlomethane. Adding methanol slowly and let sitting overnight, the title compound was precipitated out as white solid (180 mg, 39%). 1H NMR (CDCl3): δ 1.05 (6H, t, J=7.2 Hz), 2.61 (4H, q, J=7.1 Hz), 2.78 (2H, t, J=7.6 Hz), 3.10 (2H, t, J=7.6 Hz), 7.34 (2H, d, J=8.6 Hz), 7.45 (4H, m, overlapping), 7.53 (1H, s), 7.65 (2H, d, J=8.5 Hz), 8.12 (1H, s). LCMS m/z=470 (m+H+).

Workup

  1. customthe preparation of which
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with methanol
  4. filtrationThe crude solid product was collected by filtration
  5. dissolutionwas dissolved in minimum amount of dichlomethane
  6. customthe title compound was precipitated out as white solid (180 mg, 39%)

Sources & evidence

ORD record
ord-31193207ba7348d9807dbe321c9c14a9
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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