Methanol → HCID 86753557, compound

HRID 342426Notes

Reaction equation

HRID 342426 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[C:9]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:10]=3[O:11][C:12]=2[CH3:13])[N:7]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(N(CC)CC)C.CO>ClCCCl>[C:21]([NH:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[C:9]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:10]=3[O:11][C:12]=2[CH3:13])[N:7]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86753554HCID 86753554, compound

Product 1

HCID 86753557HCID 86753557, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-(2-aminothiazol-4-yl)-2-methyl-7-nitrobenzo[b]furan hydrochloride (468 mg), acetic anhydride (306 mg) and triethylamine (455 mg) in 1,2-dichloroethane (20 ml) was refluxed for 1 day. To the reaction mixture was added methanol and the mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diethyl ether to give 3-(2-acetylaminothiazol-4-yl)-2-methyl-7-nitrobenzo[b]furan (305 mg).

Workup

  1. temperaturewas refluxed for 1 day
  2. customthe mixture was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel
  4. customthe obtained oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-71c2d911847a45f09f183a91e698ae58
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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