Hydrochloric Acid → HCID 131711237, compound

HRID 1763486Notes

Reaction equation

HRID 1763486 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([O:32][CH3:33])[CH:26]=2)[CH:6]=[CH:5][C:4]=1[OH:34].[NH2:35][C:36]1[CH:37]=[C:38]([CH:42]2[S:46][C:45]3=[N:47][CH2:48][CH2:49][N:44]3[CH2:43]2)[CH:39]=[CH:40][CH:41]=1.Cl.[Cl:51][C:52]1[CH:60]=[CH:59][C:55]([C:56](Cl)=[O:57])=[CH:54][N:53]=1.[OH-].[Na+]>CO.C(Cl)Cl>[CH3:33][O:32][C:27]1[CH:26]=[C:25]([CH2:24][NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9][C:7]2[CH:6]=[CH:5][C:4]([OH:34])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:30]=[CH:29][C:28]=1[OH:31].[Cl:51][C:52]1[CH:60]=[CH:59][C:55]([C:56]([NH:35][C:36]2[CH:37]=[C:38]([CH:42]3[S:46][C:45]4=[N:47][CH2:48][CH2:49][N:44]4[CH2:43]3)[CH:39]=[CH:40][CH:41]=2)=[O:57])=[CH:54][N:53]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27821656-Chloronicotinoyl ChlorideHCID 131711239HCID 131711239, compound

Product 1

HCID 131711237HCID 131711237, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

dl-6-(m-Aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (dl-m-aminotetramisole) (42 g) was dissolved with stirring in aqueous methanol (200 ml methanol/50 ml water), and the pH was adjusted to 5 with 2N hydrochloric acid. The mixture was then cooled in an ice/water mixture and 6-chloronicotinoyl chloride (67 g--prepared as in Part A above) was added. The resulting mixture was stirred at room temperature overnight. The mixture was then diluted with methylene chloride (about 500 ml), and pH adjusted to 10 with 1N sodium hydroxide. The organic layer was separated, washed to neutrality with water, and allowed to stand, when the desired product, dl-6-(m-(6-chloronicotinoylamono)phenyl)-2,3,,5,6-tetrahydroimidazo[2,1-b]thiazole (52.6 g), m.p. 135°-138°, crystallied out. The product was filtered off. Evaporation of the filtrate produced a second crop (6.8 g) of the product.

Workup

  1. customprepared as in Part A above)
  2. additionwas added
  3. customThe organic layer was separated
  4. washwashed
  5. filtrationThe product was filtered off
  6. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-1e8cdfaeb3a44e959344e31e8880e466
Source dataset
uspto-grants-1978_09
Patent number
US04112102

Reaction notes

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