Ammonia → 2-Benzothiazolamine, 6-bromo-

HRID 910228

Reaction equation

HRID 910228 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.[O-2].[Mg+2].S(Cl)(Cl)(=O)=O.N>ClC1C=CC=CC=1.O>[NH2:11][C:9]1[S:10][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=2[N:8]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24648Sulfuryl chlorideHCID 2735620N-p-BromophenylthioureaHCID 6850729Magnesium monoxide

Product 1

HCID 851492-Benzothiazolamine, 6-bromo-Yield 49.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of N-(4-bromophenyl)thiourea (16.18 g) and magnesium oxide (1.41 g) in chlorobenzene (100 mL) was heated to 50° C., and a solution of sulfuryl chloride (8.43 mL) in chlorobenzene (9 mL) was added dropwise to the solution over 1 hour or longer, followed by stirring at 50° C. overnight. The reaction mixture was returned to room temperature, and water (20 mL) was added thereto. The pH of the mixture was adjusted to about 8 by use of concentrated aqueous ammonia, and the precipitates were recovered through filtration. The obtained solid was recrystallized from 90% ethanol, to thereby yield the title compound (7.95 g).

Workup

  1. customwas returned to room temperature
  2. filtrationthe precipitates were recovered through filtration
  3. customThe obtained solid was recrystallized from 90% ethanol

Sources & evidence

ORD record
ord-b0fd9dd3609b43099be2bb67858921e4
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Linked notes

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