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Sodium Bicarbonate → 4,5-Bis(4-methoxyphenyl)-2-(3-isopropylureidomethyl)thiazole

HRID 483979
Notes
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Reaction equation

HRID 483979 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[S:5][C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:8]=1.[C:25](=[O:28])([O-])O.[Na+].NCC1S[C:34](C2C=CC(OC)=CC=2)=[C:35]([C:37]2C=CC(OC)=CC=2)[N:36]=1>ClCCl>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[N:8]=[C:4]([CH2:3][NH:2][C:25]([NH:36][CH:35]([CH3:37])[CH3:34])=[O:28])[S:5][C:6]=2[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 99736622-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazoleHCID 197488812-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazole hydrochloride

Product 1

HCID 104317614,5-Bis(4-methoxyphenyl)-2-(3-isopropylureidomethyl)thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (1.00 g) was added to a mixture of dichloromethane and saturated aqueous sodium hydrogencarbonate, and 2-aminomethyl-4,5-bis(4-methoxyphenyl)thiazole was extracted with dichloromethane. The separated organic layer was washed with water and brine, and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo and the resulting residue was dissolved with tetrahydrofuran (20 ml) and methanol (7 ml). N-Isopropyl isocyanate (0.38 ml) was added thereto, and the reaction mixture was stirred at ambient temperature for 90 minutes. The reaction mixture was evaporated in vacuo, and the resulting powder was triturated with isopropyl ether, to give 4,5-bis(4-methoxyphenyl)-2-(3-isopropylureidomethyl)thiazole (1.04 g).

Workup

  1. extractionwas extracted with dichloromethane
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionthe resulting residue was dissolved with tetrahydrofuran (20 ml) and methanol (7 ml)
  7. additionN-Isopropyl isocyanate (0.38 ml) was added
  8. customThe reaction mixture was evaporated in vacuo
  9. customthe resulting powder was triturated with isopropyl ether

Sources & evidence

ORD record
ord-2797484b8cf749119be5bc29c6098ecb
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05229386

Reaction notes

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