6-Nitro-benzothiazol-2-yl-carbamic acid ethyl ester → 2-Amino-6-nitrobenzothiazole

HRID 1164403Notes

Reaction equation

HRID 1164403 reaction equation
C(OC(=O)NC1SC2C=CC=CC=2N=1)C.C(OC(=O)[NH:20][C:21]1[S:22][C:23]2[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:24]=2[N:25]=1)C>O>[NH2:20][C:21]1[S:22][C:23]2[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:24]=2[N:25]=1

Participants

4

Reactant 2

HCID 3319976-Nitro-benzothiazol-2-yl-carbamic acid ethyl esterHCID 854169ethyl N-(1,3-benzothiazol-2-yl)carbamate

Product 1

HCID 227042-Amino-6-nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19 g (0.09 mol) of benzothiazol-2-yl-carbamic acid ethyl ester are nitrated as described in Example 1. The resulting water-moist paste of 6-nitro-benzothiazol-2-yl-carbamic acid ethyl ester is saponified at pH 10 to 12 and the mixture is worked up, as described in Example 1. 9.8 g of 2-amino-6-nitrobenzothiazole of melting point 249° to 252° C. are obtained. The content of isomeric nitro compounds is less than 1%.

Sources & evidence

ORD record
ord-d7172455e8b94f63b221577701da8931
Source dataset
uspto-grants-1983_01
Patent number
US04369324

Reaction notes

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