Dichloromethane → HCID 23282565, compound

HRID 369880Notes

Reaction equation

HRID 369880 reaction equation
ClCCl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:31]=[CH:32][C:33]=1[O:34][CH2:35][C:36]([OH:38])=O)[C:9]([CH:11]=[P:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[NH2:39][C:40]1[S:41][C:42]2[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=2[N:44]=1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(N(CC)CC)C>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:31]=[CH:32][C:33]=1[O:34][CH2:35][C:36]([NH:39][C:40]1[S:41][C:42]2[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=2[N:44]=1)=[O:38])[C:9]([CH:11]=[P:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8706Benzo(d)thiazol-2-amineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 23282603HCID 23282603, compound

Product 1

HCID 23282565HCID 23282565, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To dichloromethane (50 ml) are added (3-methoxy-4-carboxymethoxybenzoyl)methylenetriphenylphosphorane (5 g), 2-aminobenzothiazole (1.9 g), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (2.93 g) and triethylamine (3.3 ml), and the mixture is stirred overnight. After the reaction is complete, the mixture is washed with an aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate to remove the solvent, and further recrystallized from toluene to give [3-methoxy-4-(2-benzothiazolylaminocarbonylmethoxy)benzoyl]methylenetriphenylphosphorane (5.17 g).

Workup

  1. washthe mixture is washed with an aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customto remove the solvent
  4. customfurther recrystallized from toluene

Sources & evidence

ORD record
ord-71488113d0e94b12a6a2c2e8ecfacef0
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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