Tert-Butylamine → HCID 22906430, compound

HRID 2396340Notes

Reaction equation

HRID 2396340 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([NH2:13])[CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:34]1C(=O)CCC1=O.CCOC(/N=N/C(OCC)=O)=O.[C:53](N)([CH3:56])([CH3:55])[CH3:54]>O1CCCC1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:34])=[O:10])=[C:6]([NH2:13])[C:5]=1[C:53]([CH3:56])([CH3:55])[CH3:54])([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 6385Tert-ButylamineHCID 11776TriphenylphosphineHCID 120764-Nitroanthranilic acidHCID 80170N-HydroxysuccinimideHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22906430HCID 22906430, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 4-nitro-2-aminobenzoic acid (500 mg, 2.75 mmol) in tetrahydrofuran(10 mL). Add triphenylphosphine (730 mg, 2.75 mL) and N-hydroxysuccinimide (316 mg, 2.75 mmol). Add a solution of diethylazodicarboxylate (0.433 mL,2.75 mmol) and stir at room temperature under nitrogen for 10 minutes. Add tert-butylamine (1.1 mL, 5.5 mmol) in tetrahydrofuran (5 mL) directly to the reaction to yield after workup the 4-nitro-2-amino-tert-butylbenzamide.

Sources & evidence

ORD record
ord-c666032878544b78ae5e1f98648b6b47
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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