Pyridine → Toluene-4-thiosulfonic acid S-(2-acetylamino-5-tert-butyl-benzothiazol-6-yl)ester

HRID 1859545Notes

Reaction equation

HRID 1859545 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:8]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:7][C:5]=2[N:6]=1.[C:26](Cl)(=[O:28])[CH3:27].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:26]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:8]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:7][C:5]=2[N:6]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54107741Toluene-4-thiosulfonic acid S-(2-amino-5-tert-butyl-benzothiazol-6-yl)ester

Product 1

HCID 86592608Toluene-4-thiosulfonic acid S-(2-acetylamino-5-tert-butyl-benzothiazol-6-yl)ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in Example BB-15 using toluene-4-thiosulfonic acid S-(2-amino-5-tert-butyl-benzothiazol-6-yl)ester (prepared in Example BB-1; 1.75 g, 4.47 mmol), acetyl chloride (4 mL), pyridine (5 mL), DMAP (0.3 g) and CH2Cl2 (20 mL). The crude product was purified by flash silica gel chromatography (20%-70% EtOAc in hexanes as eluents). MS(APCI): 435 (M+H).

Workup

  1. customThe crude product was purified by flash silica gel chromatography (20%-70% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-d11cae3359e147f58c0b2c2a0f27b7ec
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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