Bromine → 2-Amino-6-methoxybenzothiazole

HRID 1763842Notes

Reaction equation

HRID 1763842 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1.ClCl.BrBr>C(Cl)CCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 24526Chlorine2×HCID 6675494-Thioureidoanisole

Product 1

HCID 156302-Amino-6-methoxybenzothiazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

182 parts of p-methoxyphenyl-thiourea are suspended in ethylene chloride, and dehydrated, as described in Example 1. 35.5 parts of chlorine gas are then passed in over 1 hour at 20° C., but without addition of bromine. After stirring for a further hour, 6 parts of bromine are added, the mixture is heated to 40° C., and a further 35.5 parts of chlorine gas are introduced at this temperature over one hour. The reaction product is isolated as described in Example 1. 168 parts of 6-methoxy-2-amino-benzothiazole of melting point 160°-163° C. are thus obtained, corresponding to 93% of theory.

Workup

  1. customare then passed in over 1 hour at 20° C.
  2. customThe reaction product is isolated

Sources & evidence

ORD record
ord-a2d5469e99a244ad8b6a5085cde22ce0
Source dataset
uspto-grants-1978_09
Patent number
US04113732

Reaction notes

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