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Triethylamine → 2-Carbamyl-6-Hydroxybenzothiazole Dimethylphosphate

HRID 21722
Notes
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Reaction equation

HRID 21722 reaction equation
[C:1]([C:4]1[S:5][C:6]2[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:7]=2[N:8]=1)(=[O:3])[NH2:2].C(N(CC)CC)C.[CH3:21][O:22][P:23](Cl)([O:25]C)=[O:24]>C1COCC1>[CH3:21][O:22][P:23]([OH:25])([O:13][CH3:11])=[O:24].[C:1]([C:4]1[S:5][C:6]2[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:7]=2[N:8]=1)(=[O:3])[NH2:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 101863Phosphorochloridic acid, dimethyl esterHCID 98389112-Benzothiazolecarboxamide, 6-hydroxy-

Product 1

HCID 867487322-Carbamyl-6-Hydroxybenzothiazole Dimethylphosphate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Three grams (0.015moles) of 2-carbamyl-6-hydroxybenzothiazole (ABT) was dissolved in 30 mLs of THF. Then 1.72 g (0.017 moles) triethylamine was added to the stirring reaction solution, followed immediately by the addition over 5 minutes of 2.6 g (0.018 moles) of dimethylchlorophosphate dissolved in 7 mLs of THF. This solution was stirred for 72 hours at room temperature.

Sources & evidence

ORD record
ord-34a06c3811de450caff1736c91de2d1f
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05424440

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes