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

HRID 1730560Notes

Reaction equation

HRID 1730560 reaction equation
C[O:2][C:3]([C:5]1[NH:6][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.[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1>C1(C)C(C)=CC=CC=1>[OH:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7](=[O:20])(=[O:21])[NH:6][C:5]=1[C:3]([NH:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[O:2])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 547193904-hydroxy-2H-naphtho[2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 546959454-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

3.2 gm (0.01 mol) of 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-amino-thiazole were heated for 16 hours in 200 ml of dry xylene analogous to Example 35. After cooling, the precipitate which had formed was suction-filtered off, and the mother liquor was evaporated in vacuo, whereby another crop of crude 4-hydroxy-N-(2-thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide was obtained. The two crops of crude product were combined and recrystallized three times from acetonitrile, yielding 0.85 gm (23% of theory) of the desired compound, m.p. 238° C (decomp.).

Workup

  1. temperatureAfter cooling
  2. customthe precipitate which had formed
  3. filtrationwas suction-filtered off
  4. customthe mother liquor was evaporated in vacuo, whereby another crop of crude 4-hydroxy-N-(2-thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide
  5. customwas obtained
  6. customrecrystallized three times from acetonitrile

Sources & evidence

ORD record
ord-b0d628b37c7349428caeb62aa7dbd9be
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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