Hydrochloric Acid → HCID 20233140, compound

HRID 65469Notes

Reaction equation

HRID 65469 reaction equation
C(C1C=CC2SCCC(=O)C=2C=1)C.N(OCCC(C)C)=O.[K].[CH2:23]([C:25]1[CH:26]=[CH:27][C:28]2[S:33][CH2:32][C:31](=[N:34]O)[C:30](=[O:36])[C:29]=2[CH:37]=1)[CH3:24].Cl.NC1C(=O)C2C=C(CC)C=CC=2SC=1Cl>>[NH2:34][C:31]1[C:30](=[O:36])[C:29]2[CH:37]=[C:25]([CH2:23][CH3:24])[CH:26]=[CH:27][C:28]=2[S:33][CH:32]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 5462222PotassiumHCID 20233150HCID 20233150, compoundHCID 202331523-amino-2-chloro-6-ethyl-4H-1-benzothiopyran-4-oneHCID 73666279HCID 73666279, compound

Product 1

HCID 20233140HCID 20233140, compound

Procedure

In a manner analogous to that described in Example 1, starting from 4-ethylthiophenol there is obtained 3-(4-ethylphenylthio)-propionic acid, melting point 59°-60°, which is converted into 6-ethyl-2,3-dihydro-4H-1-benzothiopyran-4-one (red oil). This is converted into an oxime with isopentyl nitrite, and the resulting crude potassium salt of 6-ethyl-3-hydroxyimino-2,3-dihydro-4H-1-benzothiopyran-4-one is converted with concentrated hydrochloric acid into 3-amino-2-chloro-6-ethyl-4H-1-benzothiopyran-4-one, melting point 79°-81°. After hydrogenation there is obtained 3-amino-6-ethyl-4H-1-benzothiopyran-4-one having a melting point of 106°-107°.

Sources & evidence

ORD record
ord-07a916fba8e84c9896463d2aeeb72752
Source dataset
uspto-grants-1986_09
Patent number
US04614745

Reaction notes

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