Ammonia → HCID 54540894, compound

HRID 1463471Notes

Reaction equation

HRID 1463471 reaction equation
C(OC([O:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:10]=[CH:11][C:12]1[S:13][C:14]2[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[N:21]=1)=O)C.N>CO>[OH:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:10]=[CH:11][C:12]1[S:13][C:14]2[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[N:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53696964HCID 53696964, compound

Product 1

HCID 54540894HCID 54540894, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Ethoxycarbonyloxy-4-methoxystyryl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine (13.2 g) was added to a solution of 1N ammonia in methanol (600 ml), and and the whole was stirred for 3 hrs. at room temperature. The solvent was distilled off under reduced pressure and the residue was purified by a column chromatography on silica gel to give 2-(3-hydroxy-4-methoxystyryl)-5,6,7, 8-tetrahydro-4H-thiazolo [5,4-b]azepine (yield 8.74 g, 81.9%). The product (1.50 g) was converted into its hydrochloride which was recrystallized from a mixture of methanol and ethyl ether to give the title compound (0.49 g, 29.0 %). m.p. 210-211°.

Workup

  1. customat room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-ee9407dc744c4d2aac5dd2193fe4d9ba
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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