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Ammonia → 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

HRID 2238373
Notes
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Reaction equation

HRID 2238373 reaction equation
[NH3:1].[Cl:2][CH2:3][CH:4]1[C:12]2[C:11]3[CH:13]=[CH:14][C:15]([S:17](Cl)(=[O:19])=[O:18])=[CH:16][C:10]=3[C:9]([N+:21]([O-:23])=[O:22])=[CH:8][C:7]=2[N:6](C(=O)C(F)(F)F)[CH2:5]1.C([O-])([O-])=O.[Cs+].[Cs+].CO>C1COCC1.[Cl-].[Na+].O>[Cl:2][CH2:3][CH:4]1[C:12]2[C:11]3[CH:13]=[CH:14][C:15]([S:17]([NH2:1])(=[O:19])=[O:18])=[CH:16][C:10]=3[C:9]([N+:21]([O-:23])=[O:22])=[CH:8][C:7]=2[NH:6][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 10796Cesium carbonateHCID 866202591-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride

Product 1

HCID 445494021-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamideYield 96.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Conc. aqueous NH3 (0.5 mL, 7.3 mmol) was added to a solution of 116 (299 mg, 0.65 mmol) in THF (10 mL) at 0° C., and the ice bath was removed. The mixture was stirred for 7 min and then Cs2CO3 (0.55 g, 1.7 mmol) and MeOH (4 mL) were added. After stirring for a further 15 min the mixture was diluted with brine and extracted with CH2Cl2 (×3). The combined extracts were dried and evaporated to give 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide (117) (214 mg, 96%) as an orange solid. A sample was triturated with EtOAc: mp 183-187° C. (dec.); 1H NMR [(CD3)2SO] δ 8.59 (d, J=1.7 Hz, 1H), 8.03 (d, J=8.9 Hz, 1H), 7.85 (dd, J=8.9, 1.7 Hz, 1H), 7.75 (s, 1H), 7.42 (s, 2H), 6.68 (s, 1H), 4.28-4.21 (m, 1H), 3.95-3.85 (m; 2H), 3.81 (dd, J=11.2, 8.3 Hz, 1H), 3.73 (dd, J=10.4, 3.0 Hz, 1H). Anal. (C13H12ClN3O4S) C, H, N.

Workup

  1. customthe ice bath was removed
  2. stirringAfter stirring for a further 15 min the mixture
  3. extractionextracted with CH2Cl2 (×3)
  4. customThe combined extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-085245a69ad14f5dbd2331e0263601d5
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes