Dehydrothio-4-toluidine → HCID 682134, compound

HRID 1358381Notes

Reaction equation

HRID 1358381 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.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24].C(N(CC)CC)C>C(Cl)Cl>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([NH:1][C:2]1[CH:3]=[CH:4][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:6][CH:7]=1)=[O:24]

Participants

5

Reactant 3

HCID 7087Dehydrothio-4-toluidineHCID 8471TriethylamineHCID 682422-Furancarbonyl chloride

Product 1

HCID 682134HCID 682134, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Route 2: 2-(4-aminophenyl)-6-methyl benzothiazole (2.0 gm, 8.3 mmole) and 2-Furoyl chloride (1.086 gm., 8.32 mmole) were suspended in methylene chloride (30 ml, anhydrous). triethylamine (1.24 gm., 12.25 mmole) was added to the reaction mixture with stirring at room temperature for 2 days. (pH 7.0-7.2). Methylene chloride (50 ml) was added to the reaction mixture, and the reaction mixture extracted with 1 N HCl (50 ml) to separate a solid. The solid was filtered and washed with water to yield 1.3 gm. (46%) of the desired compound. The product was crystallized from MeOH to obtain 0.99 gm. mp. 238-240° C. 1H and 13C NMR were consistent with the expected product. TLC showed one spot (5% MeOH—CH2Cl2 as developing solvent on silica gel plate).

Workup

  1. extractionthe reaction mixture extracted with 1 N HCl (50 ml)
  2. customto separate a solid
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customto yield 1.3 gm

Sources & evidence

ORD record
ord-9a3f1a0c4b9f412b92fc898cdfa69e61
Source dataset
uspto-grants-2003_07
Patent number
US06596744B2

Reaction notes

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