Hydrochloric Acid → HCID 20261682, compound

HRID 465037Notes

Reaction equation

HRID 465037 reaction equation
[S-2].[Na+].[Na+].[N+:4]([C:7]1[CH:12]=[C:11]([S:13][C:14]#N)[CH:10]=[CH:9][C:8]=1[OH:16])([O-:6])=[O:5].BrC[CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].Cl>CS(C)=O.CO>[OH:16][C:8]1[CH:9]=[CH:10][C:11]([S:13][CH2:14][CH2:19][N:20]2[C:21](=[O:30])[C:22]3=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]3[C:24]2=[O:25])=[CH:12][C:7]=1[N+:4]([O-:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 14804Sodium SulfideHCID 6072264-Hydroxy-3-nitrophenyl thiocyanate

Product 1

HCID 20261682HCID 20261682, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A methanol solution (15 ml) containing sodium sulfide. 9 hydrate (3.60 g) was added to 2-nitro-4-thiocyanophenol (1.96 g), which was prepared according to the method described in U.S. Pat. No. 2,562,948 (1951), in dimethyl sulfoxide (10 ml). Then N-(2-bromoethyl)phthalimide (2.54 g) was added, and the mixture was agitated for 3 hrs at room temperature, and was poured into ice water. The pH of the solution was adjusted to 5 with diluted hydrochloric acid, and the precipitate was collected to obtain N-[2-(4-hydroxy-3-nitrophenylthio)ethyl]phthalimide (2.3 g). The compound (3.5 g) was subjected to reduction under increased pressure at 70 atm in the presence of a 5% palladium carbon catalyst, and was subsequently caused to react with cyanogen bromide to yield 2-amino-5-[2-<2-(1,3-(2H)-dioxo-1H-isoindolyl)>ethylthio]benzoxazole (2 g). The benzoxazole derivative (2 g) was heated with hydrazine hydrate to yield 2-amino-5-(2-aminoethylthio)benzoxazole (1.1 g).

Workup

  1. customwas prepared
  2. customthe precipitate was collected

Sources & evidence

ORD record
ord-e87cb3229f974cb6b22ef158a2aff0b1
Source dataset
uspto-grants-1985_10
Patent number
US04550118

Reaction notes

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