Oxalyl chloride → 2',4'-Dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide

HRID 1174981Notes

Reaction equation

HRID 1174981 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1.C(Cl)(C(Cl)=O)=O.[CH3:24][N:25]([CH3:40])[CH2:26][CH2:27][N:28]([CH3:39])[C:29]1[S:30][C:31]2[CH:37]=[C:36]([NH2:38])[CH:35]=[CH:34][C:32]=2[N:33]=1>>[ClH:1].[CH3:24][N:25]([CH3:40])[CH2:26][CH2:27][N:28]([CH3:39])[C:29]1[S:30][C:31]2[CH:37]=[C:36]([NH:38][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])=[CH:14][CH:13]=3)=[O:17])[CH:35]=[CH:34][C:32]=2[N:33]=1.[CH3:24][N:25]([CH3:40])[CH2:26][CH2:27][N:28]([CH3:39])[C:29]1[S:30][C:31]2[CH:37]=[C:36]([NH:38][C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])=[CH:10][CH:11]=3)=[O:16])[CH:35]=[CH:34][C:32]=2[N:33]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 107542792',4'-Dichloro-biphenyl-4-carboxylic acidHCID 55226563N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine

Product 2

HCID 115116562',4'-Dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amideYield 105.5%HCID 693698062',4'-Dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide hydrochloride salt

Procedure

The title compound is prepared by following Method C, using 2′,4′-dichloro-biphenyl-4-carboxylic acid (6.40 g, 23.97 mmol), (COCl)2 (7.0 mL, 79.9 mmol) and N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (4.0 g, 15.9 mmol) top afford 2′,4′-dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (4.19 g, 54%). The material is dissolved in THF (100 mL), and followed by addition of 1.0 M HCl in EtOH (8.5 mL). The resulting solid is collected to give the 4.27 g (93%) of the hydrochloride salt. LC/MS, Retention time=5.17 min; (m/z): calcd for C25H24Cl2N4OS 499.5; found: 499.0.

Sources & evidence

ORD record
ord-23c066355ed441f2908436d4da2fd9d3
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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