2-Aminothiazole → 2-ethyl-4-hydroxy-N-(2-thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730565Notes

Reaction equation

HRID 1730565 reaction equation
CO[C:3]([C:5]1[N:6]([CH2:22][CH3:23])[S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[NH2:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1>C1(C)C(C)=CC=CC=1>[CH2:22]([N:6]1[C:5]([C:3]([NH:24][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[O:4])=[C:10]([OH:11])[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7]1(=[O:21])=[O:20])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:23]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 681427532-Ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 546959332-ethyl-4-hydroxy-N-(2-thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3.3 gm (0.01 mol) of 2-ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide and 1.5 gm (0.015 mol) of 2-aminothiazole were reacted in 150 ml of xylene analogous to Example 40, yielding 1.0 gm (25% of theory) or 2-ethyl-4-hydroxy-N-(2-thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 261°-262° C (decomp.), after recrystallization from ethyl acetate.

Sources & evidence

ORD record
ord-1e7bec7265e94131970034bb63544823
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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