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Water → HCID 53994067, compound

HRID 442670
Notes
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Reaction equation

HRID 442670 reaction equation
[CH2:1]1[O:21][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][NH:10][C:9](=[O:19])[CH2:8][C:7]=3[CH:20]=[C:3]2[O:2]1.C(N(CC)CC)C.[CH3:29][N:30]=[C:31]=[O:32].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]1[O:21][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][N:10]([C:31]([NH:30][CH3:29])=[O:32])[C:9](=[O:19])[CH2:8][C:7]=3[CH:20]=[C:3]2[O:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 10221329HCID 10221329, compound

Product 1

HCID 53994067HCID 53994067, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7,8-methylenedioxy-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (130 mg, 0.46 mmol) in CH2Cl2 (5 ml) was added triethylamine (1 mL), DMAP (5 mg) and methylisocyanate (60 mg) and the mixture was stirred at 25° C. for 24 h. The reaction mixture was then poured into a separatory funnel containing water (50 mL) and the product was extracted with CH2Cl2 (3×40 mL). The combined extracts were dried over Na2SO4 and solvent removed in vacuo. Purification of the residue by chromatography (1:1 of ethyl acetate: hexane) resulted in the product as a white solid (92 mg, 59%), mp, 180°-182.5° C. 1H NMR (CDCl3) 8.60 (bs, 1H), 7.74 (m, 2H), 7.46 (m, 3H), 6.88 (s, 1H), 6.67 (s, 1H), 6.07 (bs, 1H), 6.03 (bs, 1H), 3.54 (s, 1H) 3.54 (s, 1H), 2.93 (s, 1.5H), 2.92 (s, 1.5H).

Workup

  1. additionThe reaction mixture was then poured into a separatory funnel
  2. extractionthe product was extracted with CH2Cl2 (3×40 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4 and solvent
  4. customremoved in vacuo
  5. customPurification of the residue by chromatography (1:1 of ethyl acetate: hexane)

Sources & evidence

ORD record
ord-1107249c922348afbc4ba38153966e1c
Source dataset
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05891871

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes