Dehydrothio-4-toluidine → HCID 733129, compound

HRID 339541Notes

Reaction equation

HRID 339541 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1COCC1>[CH3:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:7][CH:6]=3)[S:9][C:10]=2[CH:16]=1

Participants

5

Reactant 3

HCID 7087Dehydrothio-4-toluidineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 733129HCID 733129, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in the Amide Coupling section using 2-(4-aminophenyl)-6-methylbenzothiazole (1.0 g, 4.16 mmol) and benzoyl chloride (0.58 g, 4.16 mmol) in dry THF (10 ml) containing triethylamine (0.46 g, 4.58 mmol) to give the title compound (1.23 g, 86%) as a colourless solid after work-up.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-31a90c4be840436398e42332805561be
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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