1,1'-Thiocarbonyldiimidazole → HCID 58397468, compound

HRID 410866Notes

Reaction equation

HRID 410866 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[C:6]([NH2:12])[CH:5]=1.[F:14][C:15]([S:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24]([NH2:26])[S:25][C:21]=2[CH:20]=1)([F:17])[F:16].[C:29](N1C=CN=C1)(N1C=CN=C1)=S>C(Cl)CCl>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH3:29])[C:11]([NH:26][C:24]3[S:25][C:21]4[CH:20]=[C:19]([S:18][C:15]([F:14])([F:16])[F:17])[CH:28]=[CH:27][C:22]=4[N:23]=3)=[N:12][C:6]=2[CH:5]=1)=[O:13]

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 27359646-[(Trifluoromethyl)sulfanyl]-1,3-benzothiazol-2-amineHCID 15586064Methyl 3-amino-4-(methylamino)benzoate

Product 1

HCID 58397468HCID 58397468, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Methyl-2-(6-trifluoromethylsulfanyl-benzothiazol-2-ylamino)-1H-benzo-imidazole-5-carboxylic acid methyl ester (1.43 g) was prepared by following General Procedure D starting from 3-amino-4-methylamino-benzoic acid methyl ester (0.9 g), 6-trifluoromethylsulfanyl-benzothiazol-2-ylamine (1.25 g), 1,1′-thiocarbonyldiimidazole (1.07 g), and EDC (1.15 g). LC/MS: m/z 440. 1H NMR (DMSO-d6, 400 MHz): δ 8.23 (s, 2H), 7.89 (br, 1H), 7.76 (br, 1H), 7.69 (d, 2H), 7.54 (d, 1H), 3.88 (s, 3H), and 3.68 (s, 3H).

Sources & evidence

ORD record
ord-0b0f2d5cd3824a15a81213d0ef9f37b5
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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