Butyl Isothiocyanate → 4-Chloro-3-nitro-1-(4-methyl-2-n-butylamino-5-thiazoloyl)-benzene

HRID 848764Notes

Reaction equation

HRID 848764 reaction equation
[CH2:1]([N:5]=[C:6]=[S:7])[CH2:2][CH2:3][CH3:4].[CH2:8]([N:10](CC)C(=N)C)[CH3:9].[Cl:16][C:17]1[CH:26]=[CH:25][C:20]([C:21](=[O:24])[CH2:22]Br)=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]>C(O)(C)C>[Cl:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([C:22]2[S:7][C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[N:10][C:8]=2[CH3:9])=[O:24])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 11613Butyl IsothiocyanateHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-oneHCID 4243241N,N-Diethylethanimidamide

Product 1

HCID 131511254-Chloro-3-nitro-1-(4-methyl-2-n-butylamino-5-thiazoloyl)-benzene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The same compound is also prepared as follows: 11.5 g of n-butyl isothiocyanate are added to 11.4 g of N,N-diethyl-acetamidine, whereupon the mixture becomes exothermic. The mixture is left to stand for 1 hour at 60° and the resulting adduct is used in the following experiment. A mixture of 22.9 g of the crude product and 27.9 g of 4-chloro-3-nitro-phenacyl bromide in 200 ml of isopropanol is refluxed for 2 hours. The solution is worked up as described above, yielding 4-chloro-3-nitro-1-(4-methyl-2-n-butylamino-5-thiazoloyl)-benzene.

Workup

  1. customThe same compound is also prepared
  2. waitThe mixture is left
  3. temperatureis refluxed for 2 hours

Sources & evidence

ORD record
ord-6b81f8a6adc64f01aa1cb27e58c9f2d5
Source dataset
uspto-grants-1981_10
Patent number
US04297365

Reaction notes

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