Benzocaine → HCID 1259240, compound

HRID 367115Notes

Reaction equation

HRID 367115 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:15][C:16]#[N:17].[NH4+].[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1>>[O:6]=[C:4]1[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[S:15][C:16]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=2)=[N:17]1

Participants

5

Reactant 4

HCID 2337BenzocaineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 1259240HCID 1259240, compoundYield 85.5%

Procedure

The reaction procedure of Example 6 was followed except that 5.00 g of chloronicotinic acid, 25 ml of thionyl chloride, 2.42 g of ammonium thiocyanate and 5.24 g of ethyl 4-aminobenzoate were used. As a result, 8.88 g of ethyl 4-[(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl)amino)benzoate obtained.

Workup

  1. customThe reaction procedure of Example 6

Sources & evidence

ORD record
ord-0b3fb4664ab6481b91452aaf29d5142a
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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