4-Chlorophenol → 2-(2-Chlorophenylmercapto)-6-(2-diethylamino-ethoxy)-benzothiazole

HRID 581056Notes

Reaction equation

HRID 581056 reaction equation
ClC1C=CC=CC=1O[C:5]1[C:10]2[N:11]=[CH:12][S:13][C:9]=2[CH:8]=[C:7]([O:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:6]=1.ClC1[S:28][C:29]2[CH:35]=[C:34](OCCN(CC)CC)[CH:33]=[CH:32][C:30]=2N=1.[Cl:44]C1C=CC(O)=CC=1.CC(C)([O-])C.[K+]>>[Cl:44][C:30]1[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=1[S:28][C:12]1[S:13][C:9]2[CH:8]=[C:7]([O:14][CH2:15][CH2:16][N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[CH:6]=[CH:5][C:10]=2[N:11]=1

Participants

5

Reactant 4

HCID 46844-ChlorophenolHCID 158176322-[(2-Chloro-1,3-benzothiazol-6-yl)oxy]-N,N-diethylethan-1-amineHCID 23665647Potassium tert-butoxideHCID 1317212964-(Chlorophenoxy)-6-(2-diethylamino-ethoxy)-benzothiazole

Product 1

HCID 158176332-(2-Chlorophenylmercapto)-6-(2-diethylamino-ethoxy)-benzothiazole

Procedure

2-(4-(Chlorophenoxy)-6-(2-diethylamino-ethoxy)-benzothiazole, from 2-chloro-6-(2-diethylamino-ethoxy)-benzothiazole and 4-chlorophenol in the presence of potassium tert. butoxide, Yield: 63.7% of theory, Melting point: 60-62° C., 1H-NMR spectrum (200 MHz, DMSO-d6, signals at ppm): 0.98 (t, 6H); 2.55 (q, 4H); 2.78 (t, 2H); 4.04 (t, 2H); 7.02 (dd, 1H); 7.41-7.64 (m, 6H).

Sources & evidence

ORD record
ord-1dbb21f0729149f28a512f741edec6d1
Source dataset
uspto-grants-1999_07
Patent number
US05919807

Reaction notes

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