Tert-butyl 2,2,2-trichloroethanimidate → HCID 9896063, compound

HRID 1954296Notes

Reaction equation

HRID 1954296 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:36]=[C:35]([CH3:37])[C:20]([O:21][S:22]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[C:27]([OH:34])[CH:26]=3)(=[O:24])=[O:23])=[C:19]([CH3:38])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.ClC(Cl)(Cl)C(=N)O[C:43]([CH3:46])([CH3:45])[CH3:44]>CCOC(C)=O.C1CCCCC1>[C:43]([O:30][C:29](=[O:31])[C:28]1[CH:32]=[CH:33][C:25]([S:22]([O:21][C:20]2[C:35]([CH3:37])=[CH:36][C:17]([C:9]3[C:10]4[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][C:11]=4[C:2]([Br:1])=[C:3]4[C:8]=3[CH:7]=[CH:6][CH:5]=[CH:4]4)=[CH:18][C:19]=2[CH3:38])(=[O:24])=[O:23])=[CH:26][C:27]=1[OH:34])([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 2

HCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 9960530HCID 9960530, compound

Product 1

HCID 9896063HCID 9896063, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

At ambient temperature, to a stirred suspension of 4-[4-(9-bromo-2, 3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (1.033 g, 1.689 mmol) in EtOAc (16.89 mL) was added a solution of t-butyl 2,2,2-trichloroacetimidate (0.7690 g, 3.379 mmol) in cyclohexane (3.379 mL). After 24 h, the reaction was concentrated in vacuo, suspended in CH2Cl2 (10 mL), filtered through a 1"silica gel pad and eluted with 10% acetone/hexane. The filtrate was concentrated to give 0.778 g (69%) of the title compound as an off white solid, mp 168-172° C. 1H NMR (DMSO-d6) δ 1.57 (s, 12 H), 2.15 (s, 6 H), 2.43 (s, 3 H), 7.18 (s, 2 H), 7.45-7.55 (m, 4 H), 7.65 (t, 1 H), 7.96 (d, 1 H), 8.19 (d, 1 H), 10.75 (s, 1 H). IR (KBr) 3400, 2900, 1680, 1380 and 1140 cm-1. mass spectrum (-ESI) m/z 665/667 (M-H). Anal. Calcd. for C33H31BrO6S2 : C, 59.37; H, 4.68; N, 0.00. Found: C, 59.33; H, 4.44; N, 0.10.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. filtrationfiltered through a 1"silica gel pad
  3. washeluted with 10% acetone/hexane
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-15e2ff56dafe4726b10d52c85d6ab64e
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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