Hydrochloric Acid → HCID 14850390, compound

HRID 973828Notes

Reaction equation

HRID 973828 reaction equation
C(N(CC)CC)C.[C:8]1([C:14]([NH:27][C:28]2[S:29][CH:30]=[C:31](/[C:33](=[N:37]/[OH:38])/[C:34]([OH:36])=[O:35])[N:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[C:44](Cl)=[O:45].Cl>ClCCl>[C:8]1([C:14]([NH:27][C:28]2[S:29][CH:30]=[C:31](/[C:33](=[N:37]/[O:38][C:44]([C:40]3[O:39][CH:43]=[CH:42][CH:41]=3)=[O:45])/[C:34]([OH:36])=[O:35])[N:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 11732720HCID 11732720, compound

Product 1

HCID 14850390HCID 14850390, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (8.7 ml) was added to an ice-cooled suspension of 2-(2-triphenylmethylamino-4-thiazolyl)- 2-(Z-hydroxyimino)acetic acid (13 g) in 250 ml of anhydrous dichloromethane with stirring. The suspension turned to a clear, faint yellow solution. A solution of 2-furoyl chloride (3.3 g) in 20 ml of anhydrous dichloromethane was dropwise added under ice cooling, the resulting light brown solution was stirred at room temperature for one hour, the mixture was poured into 130 ml of ice-cooled 0.5N hydrochloric acid, and the formed crystals were collected by filtration and washed thrice with 30 ml dichloromethane, affording 5.2 g of the objective compound as colorless crystals.

Workup

  1. temperaturecooled
  2. stirringthe resulting light brown solution was stirred at room temperature for one hour
  3. filtrationthe formed crystals were collected by filtration
  4. washwashed thrice with 30 ml dichloromethane

Sources & evidence

ORD record
ord-25e9e8d0c68745bc91f7069740da6b1b
Source dataset
uspto-grants-1991_11
Patent number
US05064953

Reaction notes

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