Triethylamine → HCID 178429747, compound

HRID 1840376Notes

Reaction equation

HRID 1840376 reaction equation
[NH:1]=[C:2]=N.[CH3:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])[C:17]=1[O:29][Si](C(C)(C)C)(C)C)=S.CS(Cl)(=O)=O.C([N:44](CC)CC)C>>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]([C:2]#[N:1])[C:13]([NH:12][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]=2[CH3:4])=[NH:44])=[C:17]([OH:29])[C:18]=1[S:23]([N:26]([CH3:27])[CH3:28])(=[O:24])=[O:25]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 160435CarbodiimideHCID 23447808HCID 23447808, compound

Product 1

HCID 178429747HCID 178429747, compound

Procedure

Following the general procedure for carbodiimide formation outlined in example 12, N-(2-methyl-3-fluorophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]thiourea (330 mg, 0.62 mmol), methanesulfonyl chloride (0.12 mL, 1.38 mmol) and triethylamine (0.2 mL, 1.04 mmol) were reacted to form the desired product (320 mg, crude). 1H NMR (CDCl3) δ 0.38 (s, 6H), 1.05 (s, 9H), 2.28 (s, 3H), 2.85 (s, 6H), 6.89 (t, 1H), 6.93 (d, 1H), 7.05 (d, 1H), 7.13 (m, 1H), 7.19 (d, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-95051ef63e23445e959010aa12ac5c22
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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